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

HRID 1422522Notes

Reaction equation

HRID 1422522 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 23.3%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
110 °C

Procedure

1-(2-Amino-4-methoxy-3-chloro-phenyl)ethanone (71.55 g, 358 mmol) was dissolved in HBr (500 mL, 48% in H2O). The reaction was heated to 110° C. for 2 days. The reaction was cooled to rt then the solids were filtered. The solids were partitioned between EtOAc and ½ sat Na2CO3(aq). Organics were dried over Na2SO4, filtered and solvent removed under reduced pressure. 1-(2-Amino-3-chloro-4-hydroxy-phenyl)-ethanone (15.5 g, 16%) was isolated by silica gel chromatography as an off-white solid.

Workup

  1. temperatureThe reaction was cooled to rt
  2. filtrationthe solids were filtered
  3. customThe solids were partitioned between EtOAc and ½
  4. dry with materialOrganics were dried over Na2SO4
  5. filtrationfiltered
  6. customsolvent removed under reduced pressure

Sources & evidence

ORD record
ord-471a01ed74c344c4b9e1805298266e00
Source dataset
uspto-grants-2015_01
Patent number
US08927484B2

Reaction notes

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