Water → 7-Methoxy-4,5-dihydro-1H-benzo[D]azepin-2(3H)-one

HRID 648966Notes

Reaction equation

HRID 648966 reaction equation
Cl[CH2:2][C:3]([NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=1)=[O:4].O>C(O)C>[CH3:15][O:14][C:10]1[CH:11]=[CH:12][C:13]2[CH2:2][C:3](=[O:4])[NH:5][CH2:6][CH2:7][C:8]=2[CH:9]=1

Participants

4

Reactant 2

HCID 962WaterHCID 214755Acetamide, 2-chloro-N-(m-methoxyphenethyl)-

Product 1

HCID 135206897-Methoxy-4,5-dihydro-1H-benzo[D]azepin-2(3H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-chloroacetyl-N-(2-(3-methoxy-phenyl)-ethyl)-amine (3.1 g, 0.0136 mol) is dissolved in ethanol (270 ml) and water (1530 ml) and illuminated for 10 hours with a high pressure mercury lamp under a nitrogen atmosphere at 20°-25° C. The solution is evaporated down (to a volume of about 400 ml), mixed with sodium bicarbonate and extracted several times with ethyl acetate. The extracts are dried over magnesium sulphate, concentrated by evaporation and the residue is purified over a silica gel column with ethyl acetate as eluant.

Workup

  1. customThe solution is evaporated down (to a volume of about 400 ml),
  2. additionmixed with sodium bicarbonate
  3. extractionextracted several times with ethyl acetate
  4. dry with materialThe extracts are dried over magnesium sulphate
  5. concentrationconcentrated by evaporation
  6. customthe residue is purified over a silica gel column with ethyl acetate as eluant

Sources & evidence

ORD record
ord-73cbc105f695482ba9d70bcca9f3fa40
Source dataset
uspto-grants-1988_04
Patent number
US04737495

Reaction notes

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