Sodium Hydroxide → 2-Amino-5-chloro-2'-hydroxybenzophenone

HRID 1419053Notes

Reaction equation

HRID 1419053 reaction equation
C([NH:4][C:5]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:6]=1[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15]C)=[O:8])(=O)C.[OH-].[Na+]>Br>[NH2:4][C:5]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:6]=1[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15])=[O:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12325888N-[4-Chloro-2-(2-methoxybenzoyl)phenyl]acetamide

Product 1

HCID 5264882-Amino-5-chloro-2'-hydroxybenzophenoneYield 98.1%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A mixture of 10 g of 2-acetylamino-5-chloro-2'-methoxybenzophenone and 100 ml of 47% hydrogen bromide was heated for 2 hours under reflux. The solution was rendered neutral with sodium hydroxide, and was subjected to extraction with 200 ml of ethyl acetate. The extract solution was washed with water and dried over anhydrous magnesium sulfate; the solvent was then distilled off under reduced pressure. The residue was purified by means of silica gel column chromatography (eluent, hexane:ethyl acetate=5:1) to yield 8.0 g of 2-amino-5-chloro-2'-hydroxybenzophenone as needles.

Workup

  1. temperaturewas heated for 2 hours
  2. temperatureunder reflux
  3. extractionwas subjected to extraction with 200 ml of ethyl acetate
  4. washThe extract solution was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was then distilled off under reduced pressure
  7. customThe residue was purified by means of silica gel column chromatography (eluent, hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-f2598d51c8a4403d9904425a6975877f
Source dataset
uspto-grants-1999_03
Patent number
US05885979

Reaction notes

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