CA1110661A - 3,5-bis(acylamino)benzamides - Google Patents

3,5-bis(acylamino)benzamides

Info

Publication number: CA1110661A
Authority: CA; Canada
Prior art keywords: formula; compound; represented; amino; acylamino
Prior art date: 1975-12-22
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA268,334A

Other languages

English (en)

French (fr)

Inventor

Kenneth R. Smith

Robert E. Halvachs

Mills T. Kneller

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Mallinckrodt Inc

Original Assignee

Mallinckrodt Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1975-12-22

Filing date

1976-12-21

Publication date

1981-10-13

1976-12-21 Application filed by Mallinckrodt Inc filed Critical Mallinckrodt Inc

1981-10-13 Application granted granted Critical

1981-10-13 Publication of CA1110661A publication Critical patent/CA1110661A/en

Status Expired legal-status Critical Current

Links

229940054066 benzamide antipsychotics Drugs 0.000 title abstract description 7
150000003936 benzamides Chemical class 0.000 title description 6
150000001875 compounds Chemical class 0.000 claims abstract description 25
-1 acylamino compound Chemical class 0.000 claims abstract description 18
UUKWKUSGGZNXGA-UHFFFAOYSA-N 3,5-dinitrobenzamide Chemical compound NC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 UUKWKUSGGZNXGA-UHFFFAOYSA-N 0.000 claims abstract description 6
230000026045 iodination Effects 0.000 claims abstract description 6
238000006192 iodination reaction Methods 0.000 claims abstract description 6
239000002253 acid Substances 0.000 claims description 16
238000000034 method Methods 0.000 claims description 16
RSCMSACQRPYYRN-UHFFFAOYSA-N 3,5-diaminobenzamide Chemical compound NC(=O)C1=CC(N)=CC(N)=C1 RSCMSACQRPYYRN-UHFFFAOYSA-N 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
239000012336 iodinating agent Substances 0.000 claims description 7
239000012736 aqueous medium Substances 0.000 claims description 6
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
229910052708 sodium Inorganic materials 0.000 claims description 4
239000011734 sodium Substances 0.000 claims description 4
QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 claims description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
229910052700 potassium Inorganic materials 0.000 claims description 2
239000011591 potassium Substances 0.000 claims description 2
239000000126 substance Substances 0.000 claims description 2
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
230000000397 acetylating effect Effects 0.000 claims 2
230000010933 acylation Effects 0.000 abstract description 4
238000005917 acylation reaction Methods 0.000 abstract description 4
238000005984 hydrogenation reaction Methods 0.000 abstract description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 27
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 17
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 16
239000003795 chemical substances by application Substances 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
239000000047 product Substances 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
125000002252 acyl group Chemical group 0.000 description 7
125000004442 acylamino group Chemical group 0.000 description 7
150000004985 diamines Chemical class 0.000 description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
125000000217 alkyl group Chemical group 0.000 description 6
NNTKCVAKJIOXQL-UHFFFAOYSA-N 3,5-diamino-n-methylbenzamide Chemical compound CNC(=O)C1=CC(N)=CC(N)=C1 NNTKCVAKJIOXQL-UHFFFAOYSA-N 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
UENRXLSRMCSUSN-UHFFFAOYSA-N 3,5-diaminobenzoic acid Chemical compound NC1=CC(N)=CC(C(O)=O)=C1 UENRXLSRMCSUSN-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
229960000443 hydrochloric acid Drugs 0.000 description 4
235000011167 hydrochloric acid Nutrition 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000002002 slurry Substances 0.000 description 4
NAWJZCSEYBQUGY-UHFFFAOYSA-N 2,3-diaminobenzamide Chemical compound NC(=O)C1=CC=CC(N)=C1N NAWJZCSEYBQUGY-UHFFFAOYSA-N 0.000 description 3
KIMCGLHTSSZPNS-UHFFFAOYSA-N 2,3-dinitrobenzamide Chemical compound NC(=O)C1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O KIMCGLHTSSZPNS-UHFFFAOYSA-N 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
239000000463 material Substances 0.000 description 3
239000011707 mineral Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
YSKSBHRFPVEMDW-UHFFFAOYSA-N 2,4,6-triiodo-n-methylbenzamide Chemical compound CNC(=O)C1=C(I)C=C(I)C=C1I YSKSBHRFPVEMDW-UHFFFAOYSA-N 0.000 description 2
OBTZDIRUQWFRFZ-UHFFFAOYSA-N 2-(5-methylfuran-2-yl)-n-(4-methylphenyl)quinoline-4-carboxamide Chemical compound O1C(C)=CC=C1C1=CC(C(=O)NC=2C=CC(C)=CC=2)=C(C=CC=C2)C2=N1 OBTZDIRUQWFRFZ-UHFFFAOYSA-N 0.000 description 2
XSYOKRQNVDUCDZ-UHFFFAOYSA-N 3,5-diacetamido-n-methylbenzamide Chemical compound CNC(=O)C1=CC(NC(C)=O)=CC(NC(C)=O)=C1 XSYOKRQNVDUCDZ-UHFFFAOYSA-N 0.000 description 2
VYWYYJYRVSBHJQ-UHFFFAOYSA-N 3,5-dinitrobenzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 VYWYYJYRVSBHJQ-UHFFFAOYSA-N 0.000 description 2
SSKJPXNSENOVOD-UHFFFAOYSA-N 3-acetamido-2,4,6-triiodo-5-(sulfinylamino)benzoyl chloride Chemical compound C(C)(=O)NC=1C(=C(C(=O)Cl)C(=C(C=1I)N=S=O)I)I SSKJPXNSENOVOD-UHFFFAOYSA-N 0.000 description 2
SETVYNZSWPLKAO-UHFFFAOYSA-N 3-acetamido-5-aminobenzoic acid Chemical compound CC(=O)NC1=CC(N)=CC(C(O)=O)=C1 SETVYNZSWPLKAO-UHFFFAOYSA-N 0.000 description 2
PXAFGNQRBIXGLM-UHFFFAOYSA-N 3-acetamido-5-nitrobenzoic acid Chemical compound CC(=O)NC1=CC(C(O)=O)=CC([N+]([O-])=O)=C1 PXAFGNQRBIXGLM-UHFFFAOYSA-N 0.000 description 2
ZNVHAQRPXAQKRU-UHFFFAOYSA-N 3-amino-5-nitrobenzoic acid Chemical compound NC1=CC(C(O)=O)=CC([N+]([O-])=O)=C1 ZNVHAQRPXAQKRU-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
101100294115 Caenorhabditis elegans nhr-4 gene Proteins 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
125000001589 carboacyl group Chemical group 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
239000000203 mixture Substances 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
JJKWHOSQTYYFAE-UHFFFAOYSA-N 2-methoxyacetyl chloride Chemical compound COCC(Cl)=O JJKWHOSQTYYFAE-UHFFFAOYSA-N 0.000 description 1
ZROPMXGARKGMLY-UHFFFAOYSA-N 3,5-bis[(2-methoxyacetyl)amino]-N-methylbenzamide Chemical compound COCC(=O)NC=1C=C(C(=O)NC)C=C(C1)NC(COC)=O ZROPMXGARKGMLY-UHFFFAOYSA-N 0.000 description 1
SQAXHTDFVCGZMC-UHFFFAOYSA-N 3,5-diamino-2,4,6-triiodo-n-methylbenzamide Chemical compound CNC(=O)C1=C(I)C(N)=C(I)C(N)=C1I SQAXHTDFVCGZMC-UHFFFAOYSA-N 0.000 description 1
MBOJIAVITPGFPA-UHFFFAOYSA-N 3-acetamido-5-amino-2,4,6-triiodo-n-methylbenzamide Chemical compound CNC(=O)C1=C(I)C(N)=C(I)C(NC(C)=O)=C1I MBOJIAVITPGFPA-UHFFFAOYSA-N 0.000 description 1
XCNHOBHCZBIGJP-UHFFFAOYSA-N 3-acetamido-5-amino-2,4,6-triiodobenzoic acid Chemical compound CC(=O)NC1=C(I)C(N)=C(I)C(C(O)=O)=C1I XCNHOBHCZBIGJP-UHFFFAOYSA-N 0.000 description 1
PYPOFFJSIUFFCH-UHFFFAOYSA-N 3-amino-5-[(2-methoxyacetyl)amino]-N-methylbenzamide Chemical compound NC=1C=C(C(=O)NC)C=C(C1)NC(COC)=O PYPOFFJSIUFFCH-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001266 acyl halides Chemical class 0.000 description 1
238000007605 air drying Methods 0.000 description 1
125000005236 alkanoylamino group Chemical group 0.000 description 1
125000003368 amide group Chemical group 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000003857 carboxamides Chemical group 0.000 description 1
239000002872 contrast media Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
230000020176 deacylation Effects 0.000 description 1
238000005947 deacylation reaction Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
230000002083 iodinating effect Effects 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
OETHQSJEHLVLGH-UHFFFAOYSA-N metformin hydrochloride Chemical compound Cl.CN(C)C(=N)N=C(N)N OETHQSJEHLVLGH-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
JFZRLYPCHVXTRQ-UHFFFAOYSA-N n-methyl-3,5-dinitrobenzamide Chemical compound CNC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 JFZRLYPCHVXTRQ-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
RIBFXMJCUYXJDZ-UHFFFAOYSA-N propanoyl bromide Chemical compound CCC(Br)=O RIBFXMJCUYXJDZ-UHFFFAOYSA-N 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000011135 tin Substances 0.000 description 1
238000010792 warming Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)

CA268,334A 1975-12-22 1976-12-21 3,5-bis(acylamino)benzamides Expired CA1110661A (en)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date
US64321175A	1975-12-22	1975-12-22
US643,211		1975-12-22
US73416076A	1976-10-20	1976-10-20
US734,160		1976-10-21

Publications (1)

Publication Number	Publication Date
CA1110661A true CA1110661A (en)	1981-10-13

Family

ID=27094206

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA268,334A Expired CA1110661A (en)	1975-12-22	1976-12-21	3,5-bis(acylamino)benzamides

Country Status (9)

Country	Link
JP (1)	JPS5293739A (it)
AU (1)	AU503390B2 (it)
CA (1)	CA1110661A (it)
DE (1)	DE2658300A1 (it)
FR (1)	FR2336383A1 (it)
GB (1)	GB1505633A (it)
IT (1)	IT1069882B (it)
NL (1)	NL7614188A (it)
SE (1)	SE7614386L (it)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL117629A (en) *	1995-04-03	2000-08-13	Centaur Pharmaceuticals Inc	Pharmaceutical compositions containing a benzamide derivative and methods for the preparation thereof
US5756548A (en)	1995-04-03	1998-05-26	Centaur Pharmaceuticals, Inc.	Acetamidobenzamide compounds for neurodegenerative disorders
US5658953A (en) *	1995-04-03	1997-08-19	Centaur Pharmaceuticals, Inc.	Pharmaceutical compositions of acetamidobenzamide compounds for neurodegenerative disorders
US5643965A (en) *	1995-04-03	1997-07-01	Centaur Pharmaceuticals, Inc.	Aminobenzamide compounds for the treatment of neurodegenerative disorders
US5955506A (en) *	1996-04-03	1999-09-21	Centaur Pharmaceuticals, Inc.	Benzamides for neurodegenerative disorder treatment

1976
- 1976-12-15 IT IT69982/76A patent/IT1069882B/it active
- 1976-12-17 GB GB52802/76A patent/GB1505633A/en not_active Expired
- 1976-12-21 JP JP15296076A patent/JPS5293739A/ja active Pending
- 1976-12-21 AU AU20788/76A patent/AU503390B2/en not_active Expired
- 1976-12-21 CA CA268,334A patent/CA1110661A/en not_active Expired
- 1976-12-21 FR FR7638512A patent/FR2336383A1/fr active Granted
- 1976-12-21 NL NL7614188A patent/NL7614188A/xx not_active Application Discontinuation
- 1976-12-21 SE SE7614386A patent/SE7614386L/xx unknown
- 1976-12-22 DE DE19762658300 patent/DE2658300A1/de not_active Withdrawn

Also Published As

Publication number	Publication date
GB1505633A (en)	1978-03-30
JPS5293739A (en)	1977-08-06
FR2336383A1 (fr)	1977-07-22
AU2078876A (en)	1978-06-29
SE7614386L (sv)	1977-06-23
DE2658300A1 (de)	1977-07-07
AU503390B2 (en)	1979-08-30
IT1069882B (it)	1985-03-25
FR2336383B1 (it)	1980-08-01
NL7614188A (nl)	1977-06-24

Legal Events

Date	Code	Title	Description
1998-10-13	MKEX	Expiry

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LV10859A (lv)	1995-10-20	Panemiens 2-alkil-6-metil-N-(1'-metoksi-2'propil)anilinu iegusanai un hloracetanilinidu iegusanai no siem aniliniem
JP2937083B2 (ja)	1999-08-23	芳香族シアノメチルアミンの製法
CA1110661A (en)	1981-10-13	3,5-bis(acylamino)benzamides
EP0325892B1 (de)	1993-02-03	Verfahren zur Herstellung von halogenierten aromatischen primären Aminen
Tsuji et al.	1985	Platinum complex catalyzed synthesis of urea derivatives from nitroarenes and amines under carbon monoxide
US5068436A (en)	1991-11-26	Hydrogenation of halonitrobenzenes without dehalogenation
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CA2354773C (en)	2005-05-10	Cyanoethylation of cycloaliphatic vicinal primary diamines
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US5840967A (en)	1998-11-24	Process for the preparation of contrast agents
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JPH0753495A (ja)	1995-02-28	アミノプロピオニトリルの製法
JPS598262B2 (ja)	1984-02-23	Ｐ−フエニレンジアミンの製造方法
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US3030361A (en)	1962-04-17	Butyrolactone derivatives
BE849660A (fr)	1977-04-15	3,5-bis (acylamino) benzamides
CN101360704B (zh)	2012-10-17	制备氨基链烷酰胺的方法
JPH08151353A (ja)	1996-06-11	１−アミノ−５−ブロモナフタレンの製造方法
JPS63303958A (ja)	1988-12-12	２−アミノ−４，６−ジクロル−５−アルキルフェノ−ルの製造法