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

HRID 61630

Reaction equation

HRID 61630 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-fc159f7e15dc4e17a0f43b00764ca618
Source dataset
uspto-grants-2016_09
Patent number
US09440961B2

Linked notes

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