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

HRID 1808492Notes

Reaction equation

HRID 1808492 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-4951c9b9257148408e5a3e51450a80ce
Source dataset
uspto-grants-2013_01
Patent number
US08357693B2

Reaction notes

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