4-Aminobenzonitrile → N-(4-Cyanophenyl)-4-formylbenzamide

HRID 480935Notes

Reaction equation

HRID 480935 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[CH:19]([C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1)=[O:20]>CN(C)C1C=CN=CC=1>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([NH:1][C:25](=[O:26])[C:24]2[CH:28]=[CH:29][C:21]([CH:19]=[O:20])=[CH:22][CH:23]=2)=[CH:3][CH:4]=1)#[N:7]

Participants

5

Reactant 3

HCID 133964-AminobenzonitrileHCID 81531DiisopropylethylamineHCID 124246204-Formylbenzoyl chloride

Product 1

HCID 18766367N-(4-Cyanophenyl)-4-formylbenzamideYield 11.2%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

In the same manner as that described in Example 1(1), a reaction was carried out using commercially available 4-aminobenzonitrile (343 mg, 2.9 mmol), N,N-diisopropylethylamine (1.21 ml, 7.0 mmol), 4-formylbenzoyl chloride (561 mg, 3.33 mmol) and 4-(dimethylamino)pyridine (a catalytic amount) and the reaction mixture was treated according to a similar procedure to that described in Example 1(1) to afford an oily residue. The residue was chromatographed on a silica gel column using ethyl acetate-hexane (2:1) as the eluant to obtain 4′-cyano-4-formylbenzanilide (81 mg, yield 11%) as a pale yellow solid which was recrystallized from ethyl acetate to give pale yellow powdery crystals.

Workup

  1. additionwas treated
  2. customto afford an oily residue
  3. customThe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-1d21babc88574cde91f88ae4be47d292
Source dataset
uspto-grants-2003_11
Patent number
US06653330B2

Reaction notes

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