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

HRID 1797

Reaction equation

HRID 1797 reaction equation
[NH2:1][C:2]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12]C)=[O:5].C(=O)(O)[O-].[Na+]>Br>[NH2:1][C:2]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[OH:12])=[O:5]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 12325893(2-Amino-5-chlorophenyl)(2-methoxyphenyl)methanone

Product 1

HCID 5264882-Amino-5-chloro-2'-hydroxybenzophenoneYield 93.4%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A mixture of 2.15 g of 2-amino-5-chloro-2'-methoxybenzophenone and 20 ml of 47% hydrogen bromide was heated for 1 hour under reflux. The solution was rendered neutral with sodium bicarbonate, and subjected to extraction with 100 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=10:1) to yield 1.9 g of 2-amino-5-chloro-2'-hydroxybenzophenone as needles, m.p. 51° to 52° C.

Workup

  1. temperaturewas heated for 1 hour
  2. temperatureunder reflux
  3. extractionsubjected to extraction with 100 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=10:1)

Sources & evidence

ORD record
ord-b12632ff90da4c7fbf9aead0149dd2e8
Source dataset
uspto-grants-1998_03
Patent number
US05726306

Linked notes

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