Methanol → 2-Nitro-4-phenoxyaniline

HRID 616136Notes

Reaction equation

HRID 616136 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][C:6]=1[N+:18]([O-:20])=[O:19])(=O)C.CO.[OH-].[Na+]>O>[NH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][C:6]=1[N+:18]([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 3828525N-(2-nitro-4-phenoxy-phenyl)acetamide

Product 1

HCID 51737522-Nitro-4-phenoxyaniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-Acetamido-2-nitro-4-phenoxybenzene is treated with 20 ml. methanol and 10 ml. 5 N aqueous sodium hydroxide at 20°-25° C for one hour. The mixture is diluted with water and the crude product filtered off. Recrystallization yields 1-amino-2-nitro-4-phenoxybenzene. This latter compound is treated in accordance with the first paragraph of Example VI to afford 1-(3-methoxycarbonyl-2-thioureido)-2-nitro-4-phenoxybenzene.

Workup

  1. filtrationthe crude product filtered off
  2. customRecrystallization

Sources & evidence

ORD record
ord-26aabde1758f433da668212e71bfbf78
Source dataset
uspto-grants-1978_02
Patent number
US04072696

Reaction notes

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