1-(2-Amino-3-chloro-4-methoxyphenyl)ethanone → 1-(2-Amino-3-chloro-4-hydroxy-phenyl)-ethanone

HRID 1893694Notes

Reaction equation

HRID 1893694 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[C:6]([O:9]C)[CH:5]=[CH:4][C:3]=1[C:11](=[O:13])[CH3:12]>Br>[NH2:1][C:2]1[C:7]([Cl:8])=[C:6]([OH:9])[CH:5]=[CH:4][C:3]=1[C:11](=[O:13])[CH3:12]

Participants

3

Reactant 1

HCID 299199881-(2-Amino-3-chloro-4-methoxyphenyl)ethanone

Product 1

HCID 574451951-(2-Amino-3-chloro-4-hydroxy-phenyl)-ethanoneYield 61%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
0 °C

Procedure

1-(2-Amino-3-chloro-4-methoxyphenyl)ethanone (prepared according to Raboisson, P. J.-M. B., et al., WO2007014926, p 78; 70.7 g, 354 mmol) was stirred in 48% aq. HBr (500 mL) at 110° C. for 72 h. After the mixture was cooled to 0° C. with stirring, the solids were filtered and washed with water. The resulting solids were triturated with a saturated NaHCO3 solution (−350 mL), filtered, washed with water, and dried under vacuum to give 40 g (61% yield) of 1-(2-amino-3-chloro-4-hydroxyphenyl)ethanone as a dark brown solid.

Workup

  1. filtrationthe solids were filtered
  2. washwashed with water
  3. customThe resulting solids were triturated with a saturated NaHCO3 solution (−350 mL)
  4. filtrationfiltered
  5. washwashed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-41fbcfc0ac9b485d93b5b02fbe395104
Source dataset
uspto-grants-2013_08
Patent number
US08513186B2

Reaction notes

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