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

HRID 1380860Notes

Reaction equation

HRID 1380860 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 in a nitrogen atmosphere at 20°-25° C. with a high pressure mercury lamp. The solution is evaporated down (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. Yield: 820 mg. Mp: 152°-154° C.

Workup

  1. customThe solution is evaporated down (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-be8095c5a2534eaaaaeeb846fad92dff
Source dataset
uspto-grants-1986_04
Patent number
US04584293

Reaction notes

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