2-Methoxy-5-nitroaniline → N-(2-methoxy-5-nitrophenyl)propanamide

HRID 240917

Reaction equation

HRID 240917 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:4]=1[NH2:5].C(N(CC)CC)C.[C:20](Cl)(=[O:23])[CH2:21][CH3:22]>ClCCl>[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:4]=1[NH:5][C:20](=[O:23])[CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 74472-Methoxy-5-nitroanilineHCID 8471TriethylamineHCID 62324Propionyl chloride

Product 1

HCID 2176144N-(2-methoxy-5-nitrophenyl)propanamideYield 98.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-methoxy-5-nitroaniline (1) (10.1 g, 60.0 mmol) in 250 mL dichloromethane at 0°-5° C. was treated with triethylamine (10.0 g, 100.0 mmol) and propionyl chloride (6.7 g, 6.3 mL, 72.0 mmol) for 1 hour and 0.5 h at room temperature (RT). Normal aqueous workup and removal of solvent gave a light yellow solid which was washed with hexane/EtOAc (9:1) to yield solid N-(2-Methoxy-5-nitro-phenyl)-propionamide (2) (13.2 g, 98%).

Workup

  1. customNormal aqueous workup and removal of solvent
  2. customgave a light yellow solid which
  3. washwas washed with hexane/EtOAc (9:1)

Sources & evidence

ORD record
ord-f027d2a09ee44c4cb92ff0e7f92ae1ce
Source dataset
uspto-grants-2014_02
Patent number
US08648104B2

Linked notes

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