hexahydro-3-(3-methoxyphenyl)-1-methyl-2H-azepin-2-one → hexahydro-3-(3-hydroxyphenyl)-1-methyl-2H-azepin-2-one

HRID 1594849Notes

Reaction equation

HRID 1594849 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:15][CH2:14][CH2:13][CH2:12][N:11]([CH3:16])[C:10]2=[O:17])[CH:6]=[CH:7][CH:8]=1>Br.CCOC(C)=O>[OH:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:15][CH2:14][CH2:13][CH2:12][N:11]([CH3:16])[C:10]2=[O:17])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 2727906hexahydro-3-(3-methoxyphenyl)-1-methyl-2H-azepin-2-one

Product 1

HCID 11746121hexahydro-3-(3-hydroxyphenyl)-1-methyl-2H-azepin-2-one

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(3-Methoxy-phenyl)-1-methyl-azepan-2-one (as described in Step A above) (1.067 g, 4.58 mmol) was refluxed in 48% HBr (5 mL) for 1 h. The reaction was diluted with EtOAc, washed with H2O, brine, dried (MgSO4), and concentrated to give the title compound.

Workup

  1. washwashed with H2O, brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-7cd39238f6454b4d88e10132b10d4d03
Source dataset
uspto-grants-2001_09
Patent number
US06284755B1

Reaction notes

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