2-Methoxy-4-nitroaniline → N-(2-methoxy-4-nitrophenyl)benzamide

HRID 2233228Notes

Reaction equation

HRID 2233228 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:4]=1[NH2:5].C(N(CC)CC)C.[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1(C)C=CC=CC=1>[C:20]([NH:5][C:4]1[CH:6]=[CH:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:3]=1[O:2][CH3:1])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 73372-Methoxy-4-nitroanilineHCID 7412Benzoyl chlorideHCID 8471Triethylamine

Product 1

HCID 269057N-(2-methoxy-4-nitrophenyl)benzamideYield 77.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-methoxy-4-nitroaniline (2.23 g, 13.3 mmol), triethylamine (2.00 ml, 14.6 mmol) and benzoyl chloride (1.70 ml, 14.6 mmol) were stirred in toluene (50 ml) for 24 hours under an inert atmosphere at ambient temperature. The solid was collected by suction filtration and washed with toluene (3×50 ml) and diethyl ether (50 ml). Purification of the crude product by flash chromatography on silica gel, eluting with dichloromethane, yielded N-benzoyl 2-methoxy-4-nitroaniline (2.79 g, 77% yield) as a white solid:

Workup

  1. filtrationThe solid was collected by suction filtration
  2. washwashed with toluene (3×50 ml) and diethyl ether (50 ml)
  3. customPurification of the crude product by flash chromatography on silica gel
  4. washeluting with dichloromethane

Sources & evidence

ORD record
ord-42894eb672304bf4b68c52a76dbac524
Source dataset
uspto-grants-2010_05
Patent number
US07709479B1

Reaction notes

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