4-Chloroaniline → 4'-Chloro-4-formylbenzanilide

HRID 480947Notes

Reaction equation

HRID 480947 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH:16]([C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][CH:19]=1)=[O:17]>CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:22](=[O:23])[C:21]2[CH:25]=[CH:26][C:18]([CH:16]=[O:17])=[CH:19][CH:20]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 78124-ChloroanilineHCID 8471TriethylamineHCID 124246204-Formylbenzoyl chloride

Product 1

HCID 114142744'-Chloro-4-formylbenzanilideYield 68%

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-chloroaniline (354 mg, 2.8 mmol), triethylamine (0.7 ml, 5.0 mmol), 4-formylbenzoyl chloride (700 mg, 4.2 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′-chloro-4-formylbenzanilide (489 mg, yield 68%) as a white solid which was recrystallized from ethyl acetate-hexane to give white powdery crystals.

Workup

  1. additionwas treated

Sources & evidence

ORD record
ord-eb0afc83500d4122a4a48a72be8d0427
Source dataset
uspto-grants-2003_11
Patent number
US06653330B2

Reaction notes

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