BE644413A - - Google Patents

Info

Publication number: BE644413A
Authority: BE; Belgium
Prior art keywords: acid; desc; page number; clms page; carbon atoms
Prior art date: 1964-02-27

Application number

BE644413A

Other languages

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.)

1964-02-27

Filing date

1964-02-27

Publication date

1964-06-15

1964-02-27 Application filed filed Critical

1964-02-27 Priority to BE644413A priority Critical patent/BE644413A/fr

1964-06-15 Publication of BE644413A publication Critical patent/BE644413A/fr

Links

239000002253 acid Substances 0.000 claims description 50
229910052739 hydrogen Inorganic materials 0.000 claims description 6
-1 hydroxy, nitro, amino Chemical group 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
239000000155 melt Substances 0.000 claims description 3
150000008064 anhydrides Chemical class 0.000 claims description 2
230000003197 catalytic effect Effects 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims 5
125000000217 alkyl group Chemical group 0.000 claims 4
125000001424 substituent group Chemical group 0.000 claims 2
241001465805 Nymphalidae Species 0.000 claims 1
150000007513 acids Chemical class 0.000 claims 1
125000002947 alkylene group Chemical group 0.000 claims 1
150000001408 amides Chemical class 0.000 claims 1
125000003118 aryl group Chemical group 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
125000004430 oxygen atom Chemical group O* 0.000 claims 1
229910052757 nitrogen Inorganic materials 0.000 description 42
RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 36
229910000071 diazene Inorganic materials 0.000 description 36
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
238000009835 boiling Methods 0.000 description 8
BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 8
239000000047 product Substances 0.000 description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
238000009903 catalytic hydrogenation reaction Methods 0.000 description 4
239000000203 mixture Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
238000003756 stirring Methods 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
SQAINHDHICKHLX-UHFFFAOYSA-N 1-naphthaldehyde Chemical compound C1=CC=C2C(C=O)=CC=CC2=C1 SQAINHDHICKHLX-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
229910052698 phosphorus Inorganic materials 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
APRRQJCCBSJQOQ-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 APRRQJCCBSJQOQ-UHFFFAOYSA-N 0.000 description 1
241000428352 Amma Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
101100186433 Dictyostelium discoideum napA gene Proteins 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
241001175904 Labeo bata Species 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
101100518046 Rattus norvegicus Oasl gene Proteins 0.000 description 1
241001092459 Rubus Species 0.000 description 1
235000017848 Rubus fruticosus Nutrition 0.000 description 1
101150066742 TRI1 gene Proteins 0.000 description 1
241001125929 Trisopterus luscus Species 0.000 description 1
JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
230000004927 fusion Effects 0.000 description 1
239000007789 gas Substances 0.000 description 1
LTYRAPJYLUPLCI-UHFFFAOYSA-N glycolonitrile Chemical compound OCC#N LTYRAPJYLUPLCI-UHFFFAOYSA-N 0.000 description 1
210000004013 groin Anatomy 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000007788 liquid Substances 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
BHGADZKHWXCHKX-UHFFFAOYSA-N methane;potassium Chemical compound C.[K] BHGADZKHWXCHKX-UHFFFAOYSA-N 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
229910000069 nitrogen hydride Inorganic materials 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
239000012071 phase Substances 0.000 description 1
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
230000009466 transformation Effects 0.000 description 1
230000017105 transposition Effects 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

BE644413A 1964-02-27 1964-02-27 BE644413A (de)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
BE644413A BE644413A (de)	1964-02-27	1964-02-27

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
BE644413A BE644413A (de)	1964-02-27	1964-02-27

Publications (1)

Publication Number	Publication Date
BE644413A true BE644413A (de)	1964-06-15

Family

ID=3846023

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE644413A BE644413A (de)	1964-02-27	1964-02-27

Country Status (1)

Country	Link
BE (1)	BE644413A (de)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7423059B2 (en) *	1996-08-09	2008-09-09	Wyeth	Pharmaceutically active compounds and methods of use
US7902362B2 (en) *	2004-06-10	2011-03-08	Agency For Science, Technology & Research	DNA threading intercalators

1964
- 1964-02-27 BE BE644413A patent/BE644413A/fr unknown

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7423059B2 (en) *	1996-08-09	2008-09-09	Wyeth	Pharmaceutically active compounds and methods of use
US7902362B2 (en) *	2004-06-10	2011-03-08	Agency For Science, Technology & Research	DNA threading intercalators

Publication	Publication Date	Title
US4507488A (en)	1985-03-26	N-Pyrazolylalkylenediamine intermediates
KR900006681B1 (ko)	1990-09-17	헤테로사이클릭 화합물의 제조방법
FR2530626A1 (fr)	1984-01-27	Composes de carbostyryle
BE644413A (de)	1964-06-15
CN110963959B (zh)	2023-01-24	一种合成n-保护及非保护的3-羟基-4,4-二甲基哌啶的制备方法
US4954499A (en)	1990-09-04	Pyridazinone derivatives
US3123615A (en)	1964-03-03	Oxyphenyl
NO132666B (de)	1975-09-01
US3092660A (en)	1963-06-04	1-acyl-2-alkyl-hydrazine derivatives
US3118933A (en)	1964-01-21	N-(alpha-methyl-2, 4-dichlorophenethyl) hydroxylamine and its salts
DD258006A5 (de)	1988-07-06	Verfahren zur herstellung von hydrozon-derivaten
DE69111541T2 (de)	1996-01-18	Neue Indol- und Indolin-Verbindungen.
CH408900A (fr)	1966-03-15	Procédé de préparation de la 3-phénoxy-propylguanidine
CH445490A (de)	1967-10-31	Verfahren zur Herstellung von a-(3-Indolyl)-niederaliphatischen-säuren
JPS5842182B2 (ja)	1983-09-17	新規のプロピレン−ジアミン誘導体の製造方法
DE2409313A1 (de)	1974-09-12	Neue pyrrolyl-verbindungen und verfahren zu ihrer herstellung
EP0099815A1 (de)	1984-02-01	3-Pyridyl-5-alkoxy(oder phenoxy- oder aralkyloxy-)pyrazol-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
US2970159A (en)	1961-01-31	Hydrazine derivatives
CN114773314B (zh)	2026-05-08	一种联芳基氨基胍衍生物
CH627451A5 (en)	1982-01-15	Process for the preparation of 1-(lower aminoalkyl)-3,4-diphenyl-1H-pyrazoles
KR800001699B1 (ko)	1980-12-31	아미노-페닐-에탄올 아민의 제조방법
AT360992B (de)	1981-02-10	Verfahren zur herstellung neuer phenylazacyclo- alkane und von deren salzen und optisch aktiven verbindungen
BE666612A (de)	1965-11-03
EP1430018A1 (de)	2004-06-23	Verfahren zur herstellung von beta-alaninamiden
BE728266A (de)	1969-07-16

BE644413A - - Google Patents

Info

Links

Classifications

Landscapes

Priority Applications (1)

Applications Claiming Priority (1)

Publications (1)

Family

ID=3846023

Family Applications (1)

Country Status (1)

Cited By (2)

Cited By (2)

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