p-Anisoyl chloride → HCID 18001121, compound

HRID 478170Notes

Reaction equation

HRID 478170 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11].[CH3:12][O:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1>N1C=CC=CC=1>[OH:11][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[NH:1][C:18](=[O:19])[C:17]1[CH:21]=[CH:22][C:14]([O:13][CH3:12])=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 7477p-Anisoyl chlorideHCID 41154952-Amino-3-Nitrophenol

Product 1

HCID 18001121HCID 18001121, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Amino-3-nitrophenol (308 mg) was dissolved in 10 ml of pyridine, then 341 mg of 4-methoxybenzoyl chloride was added at 0° C. and the mixture was stirred at room temperature for 18 hours. The reaction solution was concentrated in vacuo, 20 ml of chloroform was added to the resulting residue and the mixture was again concentrated in vacuo. This operation was further repeated three times, and the residue from which the pyridine had been removed was purified by silica gel column chromatography using chloroform as an eluting solvent to give 428 mg of 2′-hydroxy-4-methoxy-6′-nitrobenzanilide.

Workup

  1. concentrationThe reaction solution was concentrated in vacuo, 20 ml of chloroform
  2. additionwas added to the resulting residue
  3. concentrationthe mixture was again concentrated in vacuo
  4. customthe residue from which the pyridine had been removed
  5. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-802b23a5cdd64dabbb0c287f9baa5ae2
Source dataset
uspto-grants-2003_11
Patent number
US06642224B1

Reaction notes

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