4-Aminophenylacetonitrile → HCID 18766358, compound

HRID 480946Notes

Reaction equation

HRID 480946 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[CH:20]([C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1)=[O:21]>CN(C)C1C=CN=CC=1>[C:7]([CH2:6][C:5]1[CH:9]=[CH:10][C:2]([NH:1][C:26](=[O:27])[C:25]2[CH:29]=[CH:30][C:22]([CH:20]=[O:21])=[CH:23][CH:24]=2)=[CH:3][CH:4]=1)#[N:8]

Participants

5

Reactant 3

HCID 770004-AminophenylacetonitrileHCID 81531DiisopropylethylamineHCID 124246204-Formylbenzoyl chloride

Product 1

HCID 18766358HCID 18766358, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

In the same manner as that described in Example 2(1), a reaction was carried out using commercially available 4-aminobenzyl cyanide (329 mg, 2.5 mmol), N,N-diisopropylethylamine (0.91 ml, 5.2 mmol), 4-formylbenzoyl chloride (350 mg, 2.1 mmol) and 4-(dimethylamino)pyridine (a catalytic amount) and the reaction mixture was treated according to a similar procedure to that described in Example 2(1) to afford 4′-(cyanomethyl)-4-formylbenzanilide (370 mg, yield 67%) as a pale yellow solid which was recrystallized from a mixture of ethyl acetate and tetrahydrofuran to give pale yellow powdery crystals.

Workup

  1. additionwas treated

Sources & evidence

ORD record
ord-749aca44e062423eb935c94d92d565c1
Source dataset
uspto-grants-2003_11
Patent number
US06653330B2

Reaction notes

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