Lithium Bromide → 3-(3-hydroxyphenyl)hexahydro-2H-azepin-2-one

HRID 2049330Notes

Reaction equation

HRID 2049330 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH:8]2[CH2:14][CH2:13][CH2:12][CH2:11][NH:10][C:9]2=[O:15])=[CH:3]1.[Br-].[Li+]>C(#N)C>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:14][CH2:13][CH2:12][CH2:11][NH:10][C:9]2=[O:15])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 82050Lithium BromideHCID 12665518hexahydro-3-(3-oxocyclohexen-1-yl)-2H-azepin-2-one

Product 1

HCID 126655233-(3-hydroxyphenyl)hexahydro-2H-azepin-2-oneYield 57.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of hexahydro-3-(3-oxocyclohexen-1-yl)-2H-azepin-2-one (20.73 g), cupric bromide (44.9 g) and lithium bromide (8.8 g) was refluxed in acetonitrile (1000 ml) for 1 hour. Evaporation of the solvent left a black gum which was triturated with an excess of 2 N sodium hydroxide solution. The resulting orange suspension was filtered through Kieselguhr, and the filtrate acidified (conc.HCl). The white suspension was extracted several times with chloroform, and the residue left on evaporation of the organic layers was crystallised from ethyl acetate to give 3-(3-hydroxyphenyl)hexahydro-2H-azepin-2-one (11.8 g) m.p. 175°-178° C.

Workup

  1. customEvaporation of the solvent
  2. waitleft a black gum which
  3. customwas triturated with an excess of 2 N sodium hydroxide solution
  4. filtrationThe resulting orange suspension was filtered through Kieselguhr
  5. extractionThe white suspension was extracted several times with chloroform
  6. waitthe residue left on evaporation of the organic layers
  7. customwas crystallised from ethyl acetate

Sources & evidence

ORD record
ord-5e65a06d1b25460786fea5b487a5eaae
Source dataset
uspto-grants-1980_04
Patent number
US04197241

Reaction notes

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