Acrylonitrile → HCID 18677418, compound

HRID 380378Notes

Reaction equation

HRID 380378 reaction equation
[CH3:1][N:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[C:4]2[CH2:11][NH:12][CH2:13][CH2:14][C:3]1=2.[C:15](#[N:18])[CH:16]=[CH2:17]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].CC(O)C>[CH3:1][N:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[C:4]2[CH2:11][N:12]([CH2:17][CH2:16][C:15]#[N:18])[CH2:13][CH2:14][C:3]1=2

Participants

5

Reactant 2

HCID 7855AcrylonitrileHCID 18677411HCID 18677411, compound

Product 1

HCID 18677418HCID 18677418, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 3776IsopropanolSolvent

Procedure

A mixture of 2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indole (0.07mol), acrylonitrile (0.14 mol) and Aliquat 336 (3 drops) in 2-propanol (150 ml) was stirred and refluxed for 30 minutes. The reaction mixture was cooled on an ice-bath and the resulting precipitate was filtered off, washed with diisopropyl ether (50 ml) and dried, yielding 14.5 g (87%) of 1,3,4,5-tetrahydro-5-methyl-2H-pyrido[4,3-b]indole-2-propanenitrile (intermediate 15).

Workup

  1. temperaturerefluxed for 30 minutes
  2. temperatureThe reaction mixture was cooled on an ice-bath
  3. filtrationthe resulting precipitate was filtered off
  4. washwashed with diisopropyl ether (50 ml)
  5. customdried

Sources & evidence

ORD record
ord-da81cb660b6f4b8e82c2a8e6008a7d5e
Source dataset
uspto-grants-2001_10
Patent number
US06303614B1

Reaction notes

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