Pyridine → 5-Methoxy-2-(3-nitrobenzoyl)aminobenzamide

HRID 1406980Notes

Reaction equation

HRID 1406980 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].N1C=CC=CC=1.[N+:19]([C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C:25](Cl)=[O:26])([O-:21])=[O:20]>C(Cl)(Cl)Cl>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:2]([NH:1][C:25](=[O:26])[C:24]2[CH:28]=[CH:29][CH:30]=[C:22]([N+:19]([O-:21])=[O:20])[CH:23]=2)=[C:3]([CH:7]=1)[C:4]([NH2:6])=[O:5]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8495Benzoyl chloride, 3-nitro-HCID 203382172-Amino-5-methoxybenzamide

Product 1

HCID 593619435-Methoxy-2-(3-nitrobenzoyl)aminobenzamideYield 133.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a suspension of 2-amino-5-methoxybenzamide (2.42 g, 14.6 mmol) and pyridine (6 mL) in CHCl3 (120 mL) was added 3-nitrobenzoyl chloride (3.0 g, 16.1 mmol). The resulting mixture was stirred at RT for 6 h. The volatiles were removed in vacuo and the resultant solid was washed with Et2O to give the 5-Methoxy-2-(3-nitrobenzoyl)aminobenzamide (6.15 g) which was taken directly on to the next step. HPLC retention time 6.58 mins.

Workup

  1. customThe volatiles were removed in vacuo
  2. washthe resultant solid was washed with Et2O

Sources & evidence

ORD record
ord-2ad16f24968445a59357ecc339cbde35
Source dataset
uspto-grants-2014_12
Patent number
US08916576B2

Reaction notes

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