Diisopropylethylamine → N-(4-cyanobenzyl)-4-formylbenzamide

HRID 480967Notes

Reaction equation

HRID 480967 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1)#[N:2].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:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH:8][C:26](=[O:27])[C:25]2[CH:29]=[CH:30][C:22]([CH:20]=[O:21])=[CH:23][CH:24]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 826084-(Aminomethyl)benzonitrileHCID 124246204-Formylbenzoyl chloride

Product 1

HCID 18766296N-(4-cyanobenzyl)-4-formylbenzamideYield 55.5%

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 4-cyanobenzylamine (329 mg, 2.5 mmol), described in J. Am. Chem. Soc., 81, 4328 (1959), 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 N-(4-cyanobenzyl)-4-formylbenzamide (308 mg, yield 56) as a white solid which was recrystallized from ethyl acetate to give white fluffy crystals.

Sources & evidence

ORD record
ord-28a3923c3b2e4f219bf0ea0f308da85c
Source dataset
uspto-grants-2003_11
Patent number
US06653330B2

Reaction notes

Loading…