3-Aminocrotonitrile → t-butyl 2-[N-(5-cyano-1,4-dihydro-2,6-dimethyi-4-(3-nitro-phenyl)pyridine-3-carbonyl)amino]-acetate

HRID 342875Notes

Reaction equation

HRID 342875 reaction equation
O=[C:2]([CH3:25])[C:3](=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=1)[C:4]([NH:6][CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[O:5].[CH3:26]/[C:27](/[NH2:31])=[CH:28]\[C:29]#[N:30]>C1(C)C=CC=CC=1>[C:29]([C:28]1[CH:15]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=2)[C:3]([C:4]([NH:6][CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[O:5])=[C:2]([CH3:25])[NH:31][C:27]=1[CH3:26])#[N:30]

Participants

4

Reactant 2

HCID 53247203-AminocrotonitrileHCID 53908936t-butyl 2-[N-[2-(3-nitrobenzylidene)-3-oxobutanoyl]amino]acetate

Product 1

HCID 70072150t-butyl 2-[N-(5-cyano-1,4-dihydro-2,6-dimethyi-4-(3-nitro-phenyl)pyridine-3-carbonyl)amino]-acetateYield 98.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A toluene solution containing 348 mg (1 mmol) of t-butyl 2-[N-[3-oxo-2-(3-nitrobenzylidene)butanoyl]amino]-acetate and 123 mg (1.5 mmol) of 3-aminocrotonitrile was refluxed for 4 hours. The reaction mixture was chromatographed on a silica gel column for purification, whereby 407 mg (98.7%) of t-butyl 2-[N-(5-cyano-1,4-dihydro-2,6-dimethyl-4-(3-nitro-phenyl)pyridine-3-carbonyl)amino]-acetate was obtained.

Workup

  1. temperaturewas refluxed for 4 hours
  2. customThe reaction mixture was chromatographed on a silica gel column for purification

Sources & evidence

ORD record
ord-4b1d1c0b3c9b48ad877c6f3f566bb06a
Source dataset
uspto-grants-1999_01
Patent number
US05859244

Reaction notes

Loading…