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US4077975A
Expired / Lapsed
US
⏱️ 0.0 years remaining
1-Vinyl-4,5,6,7-tetrahydroindole and preparation thereof
Assignee: Individual
•
Filing: 1975-10-23
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Granted: 1978-03-07
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Expires: 1995-10-23
Abstract
Abstract The present invention relates to a novel chemical compound, viz. 1-vinyl-4,5,6,7-tetrahydroindole of the formula: ##STR1## and to a method of preparing same. In accordance with the invention, the method of preparing 1-vinyl-4,5,6,7-tetrahydroindole comprises reacting cyclohexanone oxime with acetylene at a molar ratio therebetween of 1:2-5 respectively at a temperature ranging from 70° to 170° C. Said reaction is effected in the presence of a basic catalyst in an amount of from 1 to 50% by weight of cyclohexanone oxime and in polar solvents or in a mixture of polar and non-polar solvents taken in a volumetric ratio to cyclohexanone oxime of 1-25:1-10 respectively. As a result of said reaction a reaction mixture is formed containing the desired product. The desired product yield is ensured by the method of the present invention as high as 90-95%. The product requires no special purification treatment. The process is technologically simple.
Inventors
- 👤 Boris Alexandrovich Trofimov
- 👤 Alexandr Spiridonovich Atavin
- 👤 Albina Ivanovna Mikhaleva
- 👤 Gennady Alexandrovich Kalabin
- 👤 Ekaterina Grigorievna Chebatareva
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 07:53
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/02; C07D209/04; C07D209/08
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
1 words
1-vinyl-4,5,6,7-tetrahydroindole.
Claim 2
Dependent Claim
1 words
1-vinyl-4,5,6,7-tetrahydroindole.
Claim 3
Independent Claim
128 words
A method of preparing 1-vinyl-4,5,6,7-tetrahydroindole comprising reacting cyclohexanone oxime with acetylene at a molar ratio therebetween of 1:2-5 at a temperature within the range of from 70° to 170° C in the presence of a catalyst selected from the group consisting of alkali and alkaline earth metals and their oxides, hydroxides and alcoholates in an amount of from 1 to 50% by weight of cyclohexanone oxime and in a polar solvent selected from the group consisting of sulfoxides, sulfones, amidophosphates, phosphine oxides, t-butyl alcohol, t-amyl alcohol, pyridine, and mixtures thereof with a non-polar solvent selected from the group consisting of hydrocarbons and cyclic ethers, said solvent being taken in a volumetric ratio to cyclohexanone oxime of 1-25:1-10 with the formation of a reaction mixture containing the desired product.
Claim 4
Independent Claim
128 words
A method of preparing 1-vinyl-4,5,6,7-tetrahydroindole comprising reacting cyclohexanone oxime with acetylene at a molar ratio therebetween of 1:2-5 at a temperature within the range of from 70° to 170° C in the presence of a catalyst selected from the group consisting of alkali and alkaline earth metals and their oxides, hydroxides and alcoholates in an amount of from 1 to 50% by weight of cyclohexanone oxime and in a polar solvent selected from the group consisting of sulfoxides, sulfones, amidophosphates, phosphine oxides, t-butyl alcohol, t-amyl alcohol, pyridine, and mixtures thereof with a non-polar solvent selected from the group consisting of hydrocarbons and cyclic ethers, said solvent being taken in a volumetric ratio to cyclohexanone oxime of 1-25:1-10 with the formation of a reaction mixture containing the desired product.
Claim 5
Dependent Claim
81 words
A method as claimed in claim 2, wherein said reaction of cyclohexanone oxime with acetylene is effected at a molar ratio therebetween of 1:3-4 at a temperature of from 90° to 140° C with the catalyst taken in an amount of from 10 to 30% by weight of cyclohexanone oxime and a polar solvent selected from the group consisting of sulfoxides, sulfones, amidophosphates, phosphine oxides, t-butyl alcohol, t-amyl alcohol and pyridine taken in a volumetric ratio to cyclohexanone oxime of 5-10:1.
Claim 6
Dependent Claim
26 words
A method as claimed in claim 2, wherein said reaction of cyclohexanone oxime with acetylene is effected under a pressure of from 1 to 30 atm.
Claim 7
Dependent Claim
22 words
A method as claimed in claim 2, wherein said non-polar solvent is used in a volumetric ratio to cyclohexanone oxime of 1-10:1.
Claim 8
Dependent Claim
30 words
A method as claimed in claim 2, wherein the catalyst is selected from the group consisting of potassium hydroxide, sodium hydroxide, calcium oxide, potassium tert-butylate, potassium tert-amylate and metallic sodium.
Claim 9
Dependent Claim
24 words
A method as claimed in claim 2, wherein the polar solvent is selected from the group consisting of dimethylsulfoxide, diethylsulfolane, hexamethyltriamidophosphate and triethylphosphine oxide.
Claim 10
Dependent Claim
21 words
A method as claimed in claim 2, wherein the non-polar solvent is selected from the group consisting of benzene and dioxane.
References Cited (Backward Citations)
US3652585A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-03-06 | 1981-09-05 | 1982-03-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-03-06 | 1985-09-05 | 1986-03-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-03-06 | 1989-09-05 | 1990-03-07 | $7700.00 | Window Closed / Lapsed |