Water → HCID 19792167, compound

HRID 1655455Notes

Reaction equation

HRID 1655455 reaction equation
[C:1]([NH:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][C:9]=1[N+:18]([O-:20])=[O:19])(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5].[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:7]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][C:9]=2[N+:18]([O-:20])=[O:19])[C:1](=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5])=[CH:35][CH:36]=1)#[N:22]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 15019124'-(Bromomethyl)-2-cyanobiphenylHCID 14722490HCID 14722490, compound

Product 1

HCID 19792167HCID 19792167, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 4-valerylamino-3-nitrobenzoate (2.1 g), 4-(2-cyanophenyl)benzyl bromide (2.0 g) and K2CO3 (1.1 g) in DMF (20 ml) was stirred for 4 hours at room temperature. To the reaction mixture was added water, the mixture was extracted with ethyl acetate, and the organic layer was washed with water. The resultant solution was dried and concentrated to give a syrup, which was purified by column chromatography on silica gel to afford a yellow syrup (3.5 g, quantitatively).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with water
  3. dry with materialThe resultant solution was dried
  4. concentrationconcentrated
  5. customto give a syrup, which
  6. customwas purified by column chromatography on silica gel
  7. customto afford a yellow syrup (3.5 g

Sources & evidence

ORD record
ord-68428675b1fb4188ae1decb1a3fa3764
Source dataset
uspto-grants-1993_10
Patent number
US05250554

Reaction notes

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