Sodium Hydroxide → 2-Bromo-5-chloro-4-methylaniline

HRID 47846Notes

Reaction equation

HRID 47846 reaction equation
C([NH:4][C:5]1[C:10]([Br:11])=[CH:9][C:8]([CH3:12])=[C:7]([Cl:13])[CH:6]=1)(=O)C.[OH-].[Na+]>C(O)(=O)C.Cl.O>[Br:11][C:10]1[CH:9]=[C:8]([CH3:12])[C:7]([Cl:13])=[CH:6][C:5]=1[NH2:4]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 10989098N-(2-Bromo-5-chloro-4-methylphenyl)acetamide

Product 1

HCID 33346562-Bromo-5-chloro-4-methylanilineYield 94%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A solution of 4-acetamido-5-bromo-2-chlorotoluene (64 g, 0.245 mol) in glacial acetic acid (48 ml) and concentrated hydrochloric acid (96 ml) was heated at 118° C. for 24 h. The reaction mixture was allowed to cool to room temperature, diluted with water (200 ml), cooled in an ice-bath and the pH was. adjusted to 5 with a aqueous solution of NaOH (50% w/v). The precipitate was collected by filtration washed with water, and dried in vacuo over P2O5 to afford a white solid (50.7 g, 94%), mp 90° C.

Workup

  1. temperaturecooled in an ice-bath
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water
  4. dry with materialdried in vacuo over P2O5

Sources & evidence

ORD record
ord-c7d09d94b1ff4568a4eeab95febd1c90
Source dataset
uspto-grants-2004_03
Patent number
US06699861B1

Reaction notes

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