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

HRID 1463113Notes

Reaction equation

HRID 1463113 reaction equation
Cl[C:2]1[C:7](=[O:8])[CH2:6][CH2:5][CH2:4][C:3]=1[CH:9]1[CH2:15][CH2:14][CH2:13][CH2:12][N:11]([CH3:16])[C:10]1=[O:17].Br.O>C(O)(=O)C>[OH:8][C:7]1[CH:2]=[C:3]([CH:9]2[CH2:15][CH2:14][CH2:13][CH2:12][N:11]([CH3:16])[C:10]2=[O:17])[CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 28175763-(2-Chloro-3-oxocyclohex-1-enyl)-hexahydro-1-methylazepin-2-one

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent3×

Procedure

Using acetic acid as solvent. A solution of 3-(2-chloro-3-oxocyclohex-1-enyl)-hexahydro-1-methylazepin-2-one (5.12 g) in glacial acetic acid (50 ml) was treated with 48% HBr in acetic acid (2 ml). After 12 hours the reaction mixture was poured on to water and the resulting precipitate removed by filtration to yield the title compound m.p. 192°-3° C. (EtOAc).

Workup

  1. customthe resulting precipitate removed by filtration

Sources & evidence

ORD record
ord-4a5f25e5f58f4655ad01fc46ba1b8ba9
Source dataset
uspto-grants-1984_07
Patent number
US04463177

Reaction notes

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