Water → Methyl 3-[N-(2'-cyanobiphenyl-4-yl)methyl-N-valerylamino]-4-nitrobenzoate

HRID 1655460Notes

Reaction equation

HRID 1655460 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[NH:14][C:15](=[O:20])[CH2:16][CH2:17][CH2:18][CH3:19])([O-:3])=[O:2].[C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]1[CH:36]=[CH:35][C:32]([CH2:33]Br)=[CH:31][CH:30]=1)#[N:22].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]1[CH:30]=[CH:31][C:32]([CH2:33][N:14]([C:5]2[CH:6]=[C:7]([CH:12]=[CH:13][C:4]=2[N+:1]([O-:3])=[O:2])[C:8]([O:10][CH3:11])=[O:9])[C:15](=[O:20])[CH2:16][CH2:17][CH2:18][CH3:19])=[CH:35][CH:36]=1)#[N:22]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 15019124'-(Bromomethyl)-2-cyanobiphenylHCID 19792184Methyl 4-nitro-3-valerylaminobenzoate

Product 1

HCID 19792114Methyl 3-[N-(2'-cyanobiphenyl-4-yl)methyl-N-valerylamino]-4-nitrobenzoateYield 73.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 4-nitro-3-valerylaminobenzoate (1.0 g), 4-(2-cyanophenyl)benzyl bromide (0.97 g) and potassium carbonate (0.55 g) in DMF (10 ml) was stirred for two days at room temperature. To the reaction mixture was added water and the mixture was extracted with ethyl acetate. The organic layer was washed with water and dried. The solvent was distilled off, and the residue was purified by column chromatography on silica gel to afford a pale yellow oil (1.24 g, 73%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. customdried
  4. distillationThe solvent was distilled off
  5. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-116ebd6047f741ec9292c39855af649f
Source dataset
uspto-grants-1993_10
Patent number
US05250554

Reaction notes

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