CA1101862A - Traduction non-disponible - Google Patents

Traduction non-disponible

Info

Publication number: CA1101862A
Authority: CA; Canada
Prior art keywords: acid; redox; naphthostyryl; process according; chloro
Prior art date: 1976-11-17
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

CA290,854A

Other languages

English (en)

Inventor

Francesco De Feo

Massimo Stolfi

Saverio Frigerio

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.)

Aziende Colori Nazionali Affini ACNA SpA

Original Assignee

Aziende Colori Nazionali Affini ACNA SpA

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.)

1976-11-17

Filing date

1977-11-14

Publication date

1981-05-26

1977-11-14 Application filed by Aziende Colori Nazionali Affini ACNA SpA filed Critical Aziende Colori Nazionali Affini ACNA SpA

1981-05-26 Application granted granted Critical

1981-05-26 Publication of CA1101862A publication Critical patent/CA1101862A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 27
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 6
125000003386 piperidinyl group Chemical group 0.000 claims abstract description 5
125000000217 alkyl group Chemical group 0.000 claims abstract 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract 2
239000002253 acid Substances 0.000 claims description 18
QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical class ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 claims description 14
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
239000001117 sulphuric acid Substances 0.000 claims description 10
235000011149 sulphuric acid Nutrition 0.000 claims description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
-1 alkyl radical Chemical class 0.000 claims description 8
238000005576 amination reaction Methods 0.000 claims description 8
238000006243 chemical reaction Methods 0.000 claims description 8
239000000203 mixture Substances 0.000 claims description 8
239000000126 substance Substances 0.000 claims description 8
239000012429 reaction media Substances 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 7
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 5
239000003054 catalyst Substances 0.000 claims description 4
229910000359 iron(II) sulfate Inorganic materials 0.000 claims description 4
MAGVJLLHDZWQFM-UHFFFAOYSA-N n-chloro-n-methylmethanamine Chemical compound CN(C)Cl MAGVJLLHDZWQFM-UHFFFAOYSA-N 0.000 claims description 4
BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 claims description 3
CIQJWKNJDQKPPO-UHFFFAOYSA-N 1-chloropiperidine Chemical compound ClN1CCCCC1 CIQJWKNJDQKPPO-UHFFFAOYSA-N 0.000 claims description 2
CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical class [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims 4
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims 2
OOFMUZPRQRQMQF-UHFFFAOYSA-N n-chloro-n-methyl-1-phenylmethanamine Chemical compound CN(Cl)CC1=CC=CC=C1 OOFMUZPRQRQMQF-UHFFFAOYSA-N 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 4
239000012847 fine chemical Substances 0.000 abstract description 2
239000000825 pharmaceutical preparation Substances 0.000 abstract 1
229940127557 pharmaceutical product Drugs 0.000 abstract 1
125000003118 aryl group Chemical group 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
150000003951 lactams Chemical class 0.000 description 6
239000000047 product Substances 0.000 description 6
239000000243 solution Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
230000008034 disappearance Effects 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
OXTCGCGDPOLJDV-UHFFFAOYSA-N 8-aminonaphthalene-1-carboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(N)=CC=CC2=C1 OXTCGCGDPOLJDV-UHFFFAOYSA-N 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
125000003368 amide group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
150000003950 cyclic amides Chemical class 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000007429 general method Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
QXJIABOUHLYVHP-UHFFFAOYSA-N n-chloromethanamine Chemical compound CNCl QXJIABOUHLYVHP-UHFFFAOYSA-N 0.000 description 1
238000006396 nitration reaction Methods 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
238000004448 titration Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/90—Benzo [c, d] indoles; Hydrogenated benzo [c, d] indoles
- C07D209/92—Naphthostyrils

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Indole Compounds (AREA)

CA290,854A 1976-11-17 1977-11-14 Traduction non-disponible Expired CA1101862A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IT29418A/76		1976-11-17
IT2941876A IT1123076B (it)	1976-11-17	1976-11-17	Procedimento di preparazione diretta di 6-amino-benz-(cd)-indol-2-(1h)-oni-n-mono oppure n,n-disostituiti

Publications (1)

Publication Number	Publication Date
CA1101862A true CA1101862A (fr)	1981-05-26

Family

ID=11226948

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA290,854A Expired CA1101862A (fr)	1976-11-17	1977-11-14	Traduction non-disponible

Country Status (10)

Country	Link
JP (1)	JPS5363374A (fr)
BE (1)	BE860923A (fr)
CA (1)	CA1101862A (fr)
CH (1)	CH629775A5 (fr)
DE (1)	DE2750681A1 (fr)
ES (1)	ES464204A1 (fr)
FR (1)	FR2392976A1 (fr)
GB (1)	GB1595090A (fr)
IT (1)	IT1123076B (fr)
NL (1)	NL7712426A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2020210630A1 (fr) *	2019-04-12	2020-10-15	C4 Therapeutics, Inc.	Agents de dégradation tricycliques d'ikaros et d'aiolos

1976
- 1976-11-17 IT IT2941876A patent/IT1123076B/it active
1977
- 1977-11-11 NL NL7712426A patent/NL7712426A/xx not_active Application Discontinuation
- 1977-11-12 DE DE19772750681 patent/DE2750681A1/de not_active Withdrawn
- 1977-11-14 CA CA290,854A patent/CA1101862A/fr not_active Expired
- 1977-11-14 JP JP13579177A patent/JPS5363374A/ja active Pending
- 1977-11-14 GB GB4736277A patent/GB1595090A/en not_active Expired
- 1977-11-14 CH CH1389477A patent/CH629775A5/it not_active IP Right Cessation
- 1977-11-16 FR FR7734445A patent/FR2392976A1/fr not_active Withdrawn
- 1977-11-16 ES ES464204A patent/ES464204A1/es not_active Expired
- 1977-11-17 BE BE182697A patent/BE860923A/fr unknown

Also Published As

Publication number	Publication date
JPS5363374A (en)	1978-06-06
BE860923A (fr)	1978-05-17
CH629775A5 (en)	1982-05-14
ES464204A1 (es)	1978-07-16
IT1123076B (it)	1986-04-30
NL7712426A (nl)	1978-05-19
GB1595090A (en)	1981-08-05
FR2392976A1 (fr)	1978-12-29
DE2750681A1 (de)	1978-05-18

Legal Events

Date	Code	Title	Description
1998-05-26	MKEX	Expiry

Publication	Publication Date	Title
US2937204A (en)	1960-05-17	Nu-alkanoyl dinitrobenzamides
US6462227B2 (en)	2002-10-08	Stabilized o-iodoxybenzoic acid compositions and process for the preparation thereof
JPS59227870A (ja)	1984-12-21	新規２−グアニジノチアゾリン誘導体ならびにその製造法
US4963679A (en)	1990-10-16	Process for preparing bis (3,5-dioxopiperazinyl) alkanes or alkenes
JPS615066A (ja)	1986-01-10	マレイミド類の製造方法
CA1101862A (fr)	1981-05-26	Traduction non-disponible
EP0253788B1 (fr)	1992-01-29	Procédé de préparation de l'acide amino-5 salicylique
US5162584A (en)	1992-11-10	Fluorobenzene derivatives
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CN117658866B (zh)	2026-02-03	一种叠氮氨基酸衍生物的合成方法
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US5144038A (en)	1992-09-01	Process for the production of 2-hydroxy-3-halo-5-nitropyridines
CA1061798A (fr)	1979-09-04	Preparation de 2-alkoxy-6-aminobenzamides
US5300688A (en)	1994-04-05	Method for making hydrazide or hydrazine compounds
RU2205821C1 (ru)	2003-06-10	Способ получения 3-нитро-4-аминотолуола
SE447106B (sv)	1986-10-27	Forfarande for framstellning av 10-oxo-10, 11-dihydro-5h-dibens /b,f/azepin-5-karboxamid
US4952697A (en)	1990-08-28	Process for the preparation of 2-nitro-3-aminopyridine, and the intermediates which are formed in the reaction
CA1176274A (fr)	1984-10-16	Methode de preparation de 5-nitro-aceto-2,4-xylidine
JPH0225430A (ja)	1990-01-26	芳香族ニトロ基の還元方法
US2310172A (en)	1943-02-02	Vitamin b6 intermediate
CA1238641A (fr)	1988-06-28	Preparation de 1-alcoyl-3,5-diphenylpyrazoles
JP2725080B2 (ja)	1998-03-09	ニトロアニリン類の製法