CH253710A - Verfahren zur Darstellung von 5,6,7,8-Tetrahydroisochinolin. - Google Patents

Verfahren zur Darstellung von 5,6,7,8-Tetrahydroisochinolin.

Info

Publication number: CH253710A
Authority: CH; Switzerland
Prior art keywords: tetrahydroisoquinoline; oxy; parts; solution; preparation
Prior art date: 1947-02-12

Application number

CH1990747A

Other languages

German (de)

English (en)

Inventor

Hoffmann-La Roche & Co. Aktiengesellschaft F.

Original Assignee

Hoffmann La Roche

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.)

1947-02-12

Filing date

1947-02-12

Publication date

1948-03-31

1947-02-12 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1947-02-12 Priority to CH1990747A priority Critical patent/CH253710A/de

1948-01-20 Priority to DK20548A priority patent/DK71267C/da

1948-02-04 Priority to FR1007638D priority patent/FR1007638A/fr

1948-02-10 Priority to ES0182226A priority patent/ES182226A1/es

1948-03-31 Publication of CH253710A publication Critical patent/CH253710A/de

1948-06-25 Priority to AT165070D priority patent/AT165070B/de

1949-11-26 Priority to DEH632A priority patent/DE833649C/de

Links

HTMGQIXFZMZZKD-UHFFFAOYSA-N 5,6,7,8-tetrahydroisoquinoline Chemical compound N1=CC=C2CCCCC2=C1 HTMGQIXFZMZZKD-UHFFFAOYSA-N 0.000 title claims description 8
238000000034 method Methods 0.000 title claims description 5
238000002360 preparation method Methods 0.000 title claims description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 3
150000007513 acids Chemical class 0.000 claims description 3
239000012320 chlorinating reagent Substances 0.000 claims description 3
IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 claims description 2
238000005984 hydrogenation reaction Methods 0.000 claims description 2
150000004800 hydroisoquinoline derivatives Chemical class 0.000 claims description 2
239000000243 solution Substances 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
229910052739 hydrogen Inorganic materials 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
238000003756 stirring Methods 0.000 description 3
ANGNQXZJVZVJMX-UHFFFAOYSA-N 3-chloro-5,6,7,8-tetrahydroisoquinoline Chemical compound C1CCCC2=C1C=C(Cl)N=C2 ANGNQXZJVZVJMX-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
239000013067 intermediate product Substances 0.000 description 2
239000000155 melt Substances 0.000 description 2
KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000007127 saponification reaction Methods 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
OHPIUROCJFAIGC-UHFFFAOYSA-N 2-(aminomethylidene)cyclohexan-1-one Chemical compound NC=C1CCCCC1=O OHPIUROCJFAIGC-UHFFFAOYSA-N 0.000 description 1
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 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000006114 decarboxylation reaction Methods 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
239000012458 free base Substances 0.000 description 1
239000000446 fuel Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
239000000203 mixture Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
229940127557 pharmaceutical product Drugs 0.000 description 1
229910052573 porcelain Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000002966 varnish Substances 0.000 description 1
238000010792 warming Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/24—Oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Other In-Based Heterocyclic Compounds (AREA)

CH1990747A 1947-02-12 1947-02-12 Verfahren zur Darstellung von 5,6,7,8-Tetrahydroisochinolin. CH253710A (de)

Priority Applications (6)

Application Number	Priority Date	Filing Date	Title
CH1990747A CH253710A (de)	1947-02-12	1947-02-12	Verfahren zur Darstellung von 5,6,7,8-Tetrahydroisochinolin.
DK20548A DK71267C (da)	1947-02-12	1948-01-20	Fremgangsmåde til fremstilling af 5,6,7,8-tetrahydroisokinolin.
FR1007638D FR1007638A (fr)	1947-02-12	1948-02-04	Procédé de préparation de la 5, 6, 7, 8-tétrahydroisoquinoléine
ES0182226A ES182226A1 (es)	1947-02-12	1948-02-10	PROCEDIMIENTO DE PREPARACIoN DE LA 5,6,7,8- TETRAHIDROISOQUINOLEiNA
AT165070D AT165070B (de)	1947-02-12	1948-06-25	Verfahren zur Darstellung des neuen 5,6,7,8-Tetrahydroisochinolins
DEH632A DE833649C (de)	1947-02-12	1949-11-26	Verfahren zur Herstellung von 5, 6, 7, 8-Tetrahydroisochinolin

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1990747A CH253710A (de)	1947-02-12	1947-02-12	Verfahren zur Darstellung von 5,6,7,8-Tetrahydroisochinolin.

Publications (1)

Publication Number	Publication Date
CH253710A true CH253710A (de)	1948-03-31

Family

ID=38463688

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1990747A CH253710A (de)	1947-02-12	1947-02-12	Verfahren zur Darstellung von 5,6,7,8-Tetrahydroisochinolin.

Country Status (6)

Country	Link
AT (1)	AT165070B (da)
CH (1)	CH253710A (da)
DE (1)	DE833649C (da)
DK (1)	DK71267C (da)
ES (1)	ES182226A1 (da)
FR (1)	FR1007638A (da)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2638472A (en) *	1949-08-26	1953-05-12	Hoffmann La Roche	1-benzyl-5, 6, 7, 8-tetrahydroisoquinoline and derivatives thereof
US2651637A (en) *	1949-12-12	1953-09-08	Bayer Ag	1-benzyl-2, 3, 5, 6, 7, 8-hexahydroisoquinolone-3 and the preparation thereof
US2651634A (en) *	1949-12-12	1953-09-08	Bayer Ag	Process for the preparation of 1-benzyl-5, 6, 7, 8-tetrahydroisoquinoline
DE912812C (de) *	1950-01-03	1954-06-03	Bayer Ag	Verfahren zur Herstellung von 1-Benzyl-bz-tetrahydro-isochinolin

1947
- 1947-02-12 CH CH1990747A patent/CH253710A/de unknown
1948
- 1948-01-20 DK DK20548A patent/DK71267C/da active
- 1948-02-04 FR FR1007638D patent/FR1007638A/fr not_active Expired
- 1948-02-10 ES ES0182226A patent/ES182226A1/es not_active Expired
- 1948-06-25 AT AT165070D patent/AT165070B/de active
1949
- 1949-11-26 DE DEH632A patent/DE833649C/de not_active Expired

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2638472A (en) *	1949-08-26	1953-05-12	Hoffmann La Roche	1-benzyl-5, 6, 7, 8-tetrahydroisoquinoline and derivatives thereof
US2651637A (en) *	1949-12-12	1953-09-08	Bayer Ag	1-benzyl-2, 3, 5, 6, 7, 8-hexahydroisoquinolone-3 and the preparation thereof
US2651634A (en) *	1949-12-12	1953-09-08	Bayer Ag	Process for the preparation of 1-benzyl-5, 6, 7, 8-tetrahydroisoquinoline
DE912812C (de) *	1950-01-03	1954-06-03	Bayer Ag	Verfahren zur Herstellung von 1-Benzyl-bz-tetrahydro-isochinolin

Also Published As

Publication number	Publication date
DE833649C (de)	1952-03-10
AT165070B (de)	1950-01-10
FR1007638A (fr)	1952-05-08
DK71267C (da)	1950-07-24
ES182226A1 (es)	1948-04-16

Publication	Publication Date	Title
CH253710A (de)	1948-03-31	Verfahren zur Darstellung von 5,6,7,8-Tetrahydroisochinolin.
DE668489C (de)	1938-12-05	Verfahren zur Darstellung von 2, 4-Dioxo-3, 3-dialkyltetrahydropyridin-6-carbonsaeureestern bzw. der entsprechenden freien Saeuren
DE422036C (de)	1925-11-23	Verfahren zur Darstellung von substituierten Ketopolyhydronaphthalinen
DE2008332C3 (de)	1980-05-22	2-Methyl-S-methoxy-3-indolylacetohydroxamsäuren, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE541316C (de)	1934-06-30	Verfahren zur Herstellung von Estern oder AEthern halogenierter Carvacrole
DE629054C (de)	1936-04-22	Verfahren zur Herstellung von Abkoemmlingen tertiaerer aliphatischer Aminosaeuren
DE924450C (de)	1955-03-03	Verfahren zur Herstellung von Cumarinderivaten
DE659638C (de)	1938-05-10	Verfahren zur Herstellung von Orthooxycarbonsaeuren der Anthrachinonreihe
DE536891C (de)	1931-10-28	Verfahren zur Darstellung von Pyridinderivaten
CH312531A (de)	1955-12-31	Verfahren zur Herstellung eines Pyridazons.
DE37727C (de)		Verfahren zur Darstellung von Verbindungen der Lävulinsäure mit den aromatischen Hydrazinen
DE439290C (de)	1927-01-08	Vefahren zur Herstellung von Naphthooxythiophenen
DE579225C (de)	1933-06-22	Verfahren zur Darstellung von 3, 4, 5-Trihalogenpyridin-2, 6-dicarbonsaeuren
DE438326C (de)	1926-12-21	Verfahren zur Darstellung von Derivaten des Methylhydrastinins
AT106480B (de)	1927-05-25	Verfahren zur Darstellung eines jodsubstituierten Oxindols.
DE563259C (de)	1932-11-03	Verfahren zur Darstellung von basischen Abkoemmlingen des Guajacols
DE652041C (de)	1937-10-23	Verfahren zur Herstellung von 4-Phenylisochinolin und Abkoemmlingen desselben
DE488680C (de)	1930-01-09	Verfahren zur Darstellung basischer Derivate der Nitro-9-aminoacridine
DE423026C (de)	1925-12-18	Verfahren zur Darstellung eines Bz-Tetrahydrooxychinolins
DE586247C (de)	1933-10-19	Verfahren zur Gewinnung von basischen Estern fettaromatischer Saeuren
DE668628C (de)	1938-12-07	Verfahren zur Darstellung von Alkyl- und Aralkylabkoemmlingen der 3,4-Cyclotetramethylen-1-aryl-5-pyrazolone
DE648062C (de)	1937-07-21	Verfahren zur Herstellung von Barbitursaeureabkoemmlingen
AT203004B (de)	1959-04-25	Verfahren zur Herstellung von neuen Estern des Piperidyl-(2)-phenylcarbinols und von deren Salzen
AT202145B (de)	1959-02-10	Verfahren zur Herstellung von substituierten 2-Oxo-benzo-chinolizinen
DE421387C (de)	1925-11-11	Verfahren zur Darstellung von reinem ª‡-Sparteinjodmethylat

CH253710A - Verfahren zur Darstellung von 5,6,7,8-Tetrahydroisochinolin. - Google Patents

Info

Links

Classifications

Landscapes

Priority Applications (6)

Applications Claiming Priority (1)

Publications (1)

Family

ID=38463688

Family Applications (1)

Country Status (6)

Cited By (4)

Cited By (4)

Also Published As

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