Sodium Hydroxide → 4-(Methoxymethoxy)-2-nitroaniline

HRID 616131Notes

Reaction equation

HRID 616131 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][O:13][CH3:14])=[CH:7][C:6]=1[N+:15]([O-:17])=[O:16])(=O)C.[OH-].[Na+]>CO.O>[NH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][O:13][CH3:14])=[CH:7][C:6]=1[N+:15]([O-:17])=[O:16]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 20371082N-[4-(Methoxymethoxy)-2-nitrophenyl]acetamide

Product 1

HCID 185092024-(Methoxymethoxy)-2-nitroaniline

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The resulting 1-acetamido-4-methoxymethoxy-2-nitro-benzene is treated with sodium hydroxide in methanol, warmed briefly on a steam bath for about 15 minutes until the reaction is complete, diluted with water and extracted with dichloromethane to afford 1-amino-4methoxymethoxy-2-nitrobenzene. This latter compound is treated in accordance with the first paragraph of Example VI to afford 1-(3-methoxycarbonyl-2-thioureido)-4-methoxymethoxy-2-nitrobenzene. This latter compound is reduced in accordance with the iron reduction technique as set forth in the third paragraph of Example XIX to afford 2-amino-1-(3-methoxycarbonyl-2-thioureido)-4-methoxymethoxybenzene. This latter compound is treated in accordance with the first paragraph of Example XVI to afford 2-acetamido-1-(3-methoxycarbonyl-2-thioureido)-4-methoxymethoxybenzene.

Workup

  1. temperaturewarmed briefly on a steam bath for about 15 minutes until the reaction
  2. extractionextracted with dichloromethane

Sources & evidence

ORD record
ord-54e1013d8cab4805985152233eb5ca2d
Source dataset
uspto-grants-1978_02
Patent number
US04072696

Reaction notes

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