Sodium Hydroxide → 4-Bromo-2-nitroaniline

HRID 581949Notes

Reaction equation

HRID 581949 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:6]=1[N+:12]([O-:14])=[O:13])(=O)C.[OH-].[Na+]>C(COC)OC>[Br:11][C:8]1[CH:9]=[CH:10][C:5]([NH2:4])=[C:6]([N+:12]([O-:14])=[O:13])[CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 136690N-(4-bromo-2-nitrophenyl)acetamide

Product 1

HCID 701324-Bromo-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1d (3.5 g, 13.5 mmol), dimethoxyethane (100 ml) and aqueous sodium hydroxide (50 ml, 1 M) is heated to 80° C. for 1 hour. After cooling the mixture is poured into ice-water. The product is filtered off, washed with water and dried. Yield 2.77 g (94%). Mp 109-1 10° C.

Workup

  1. temperatureAfter cooling the mixture
  2. filtrationThe product is filtered off
  3. washwashed with water
  4. customdried
  5. customMp 109-1 10° C.

Sources & evidence

ORD record
ord-ce5c175808de4d54af57312909f4641a
Source dataset
uspto-grants-1999_07
Patent number
US05922724

Reaction notes

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