Toluene → 3-Amino-3-(4-methoxyphenyl)-2-methylprop-2-enenitrile

HRID 2422698Notes

Reaction equation

HRID 2422698 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1.CC(C)([O-])C.[K+].[C:17](#[N:20])[CH2:18][CH3:19].C1(C)C=CC=CC=1>C([O-])(O)=O.[Na+]>[NH2:8][C:7]([C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[C:18]([CH3:19])[C:17]#[N:20]

Participants

6

Reactant 4

HCID 1140TolueneHCID 7854PropionitrileHCID 701294-MethoxybenzonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 534010953-Amino-3-(4-methoxyphenyl)-2-methylprop-2-enenitrileYield 35.1%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

Combine 4-methoxybenzonitrile (50.0 g, 376 mmol), potassium t-butoxide (84.2 g, 752 mmol), propionitrile (62.0 g, 1.130 mmol) and toluene (1,880 mL); and stir for 72 h. Dilute with satd NaHCO3 and extract with EtOAc. Evaporate the organic solution and crystallize from hexane/EtOAc to afford 3-amino-3-(4-methoxyphenyl)-2-methylacrylonitrile. Yield: 35.1%. ES-MS: m/e 189.2 (m+1).

Workup

  1. extractionextract with EtOAc
  2. customEvaporate the organic solution
  3. customcrystallize from hexane/EtOAc

Sources & evidence

ORD record
ord-3eb7fefc770b4bd8badc53159cfb4274
Source dataset
uspto-grants-2011_06
Patent number
US07960419B2

Reaction notes

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