Acetic Acid → 6-methoxy-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one

HRID 1759309Notes

Reaction equation

HRID 1759309 reaction equation
C1(S(O)(=O)=[O:8])C=CC=CC=1.[CH3:11][O:12][C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[CH2:15][CH2:16][CH2:17][C:18]2=[N:23]O.C(O)(=O)C>O>[CH3:11][O:12][C:13]1[C:14]2[CH2:15][CH2:16][CH2:17][C:18](=[O:8])[NH:23][C:19]=2[CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 86738501HCID 86738501, compound

Product 1

HCID 99423616-methoxy-4,5-dihydro-1H-benzo[b]azepin-2(3H)-oneYield 75.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

9.7 g (0.029 mole) of 5-methoxy-tetralone-1-oxime benzenesulfonate in 800-900 ml of 50% strength acetic acid are kept on a waterbath until completely dissolved (about 60 minutes). The solution is then diluted with twice its volume of water and the mixture is repeatedly extracted with ether. The combined ether extracts are washed first with aqueous bicarbonate solution and then repeatedly with water, and are dried and concentrated. The residue which remains crystallizes on being left to stand, and is analytically pure. 4.2 g of 6-methoxy-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one (75.7% yield), of melting point 162° C., are obtained.

Workup

  1. dissolutionuntil completely dissolved (about 60 minutes)
  2. extractionthe mixture is repeatedly extracted with ether
  3. washThe combined ether extracts are washed first with aqueous bicarbonate solution
  4. dry with materialrepeatedly with water, and are dried
  5. concentrationconcentrated
  6. customThe residue which remains crystallizes
  7. waiton being left

Sources & evidence

ORD record
ord-5182d3c1477f45fa996f3d51af471f06
Source dataset
uspto-grants-1982_07
Patent number
US04340595

Reaction notes

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