Acrylonitrile → HCID 68757669, compound

HRID 1465414Notes

Reaction equation

HRID 1465414 reaction equation
[CH:1]1[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[NH:6][C:5]=2[CH:4]=[CH:3][N:2]=1.[C:14](#[N:17])[CH:15]=[CH2:16].[OH-].[CH2:19]([N+](C)(C)C)C1C=CC=CC=1>C1C=CC=CC=1>[CH3:19][N:2]1[CH2:3][CH2:4][C:5]2[N:6]([CH2:16][CH2:15][C:14]#[N:17])[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:13]=2[CH2:1]1

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 66854Benzyltrimethylammonium hydroxideHCID 130802gamma-Carboline

Product 1

HCID 68757669HCID 68757669, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of Pyrido[4,3-b]indole G3-a (R19=H) (2.108 g, 11.3 mmol) in mixture benzene (30 ml) and acrylonitrile (10 mL) was added benzyltrimethylammonium hydroxide solution (40% wt. % in methanol, 0.7 mL). The mixture was heated under reflux for 1 h, cooled, washed with water, dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (benzene/Et3N, 9:1) gave 2.174 g (80%) of the title compound, mp 108-110° C. (acetone, −12° C.). 1H NMR (Acetone-d6): 2.46 (3H, s), 2.73-3.01 (6H, m), 3.56 (2H, s), 4.48 (2H, t), 6.97-7.16 (2-H, m), 7.38 (1H, d), 7.45 (1H, d).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1 h
  3. temperaturecooled
  4. washwashed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customPurification by column chromatography on silica gel (benzene/Et3N, 9:1)

Sources & evidence

ORD record
ord-7937d6735f584595b0fa926393211260
Source dataset
uspto-grants-2015_04
Patent number
US08999978B2

Reaction notes

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