Acetic Anhydride → HCID 86733859, compound

HRID 1283981Notes

Reaction equation

HRID 1283981 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]2[CH2:16][C@H:15]3[C@H:10]([CH2:11][CH2:12][CH2:13][NH:14]3)[C:9]([CH3:18])([CH3:17])[C:8]=2[CH:19]=1.O.O.O.[C:23]([O-])(=[O:25])[CH3:24].[Na+].C(OC(=O)C)(=O)C>>[C:23]([N:14]1[C@@H:15]2[C@@H:10]([C:9]([CH3:17])([CH3:18])[C:8]3[CH:19]=[C:4]([O:3][CH3:2])[CH:5]=[CH:6][C:7]=3[CH2:16]2)[CH2:11][CH2:12][CH2:13]1)(=[O:25])[CH3:24]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 23665404Sodium Acetate TrihydrateHCID 86733860HCID 86733860, compound

Product 1

HCID 86733859HCID 86733859, compound

Procedure

A mixture of 0.56 g. of cis-1,2,3,4,4a,5,10,10a-octahydro-7-methoxy-5,5-dimethylbenzo[g]quinoline hydrochloride, 0.27 g. of sodium acetate trihydrate, and 7 ml. of acetic anhydride was stirred and heated on a steam bath for three hours. The reaction mixture was evaporated to dryness under reduced pressure, and the resulting residue was partitioned between water and diethyl ether. The ether layer was washed with 1N-hydrochloric acid and with saturated aqueous sodium bicarbonate solution. After drying the ethereal solution, filtering, and removing the solvent by evaporation under reduced pressure, there was obtained 0.52 g. of a syrup which crystallized from hexane to yield cis-1-acetyl-1,2,3,4,4 a,5,10,10a-octahydro-7-methoxy-5,5-dimethylbenzo[g]quinoline, m.p. 81°-85°C; ir (CHCl3), 1630 cm.-1 (C=O); nmr (CDCl3), 80 (s,3), 78 (s,3).

Workup

  1. additionA mixture of 0.56 g
  2. temperatureheated on a steam bath for three hours
  3. customThe reaction mixture was evaporated to dryness under reduced pressure
  4. customthe resulting residue was partitioned between water and diethyl ether
  5. washThe ether layer was washed with 1N-hydrochloric acid and with saturated aqueous sodium bicarbonate solution
  6. customAfter drying the ethereal solution
  7. filtrationfiltering
  8. customremoving the solvent
  9. customby evaporation under reduced pressure
  10. customthere was obtained 0.52 g
  11. customof a syrup which crystallized from hexane

Sources & evidence

ORD record
ord-bf3c1638d3274b08ac142b645ea30692
Source dataset
uspto-grants-1976_08
Patent number
US03976653

Reaction notes

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