Acetic Anhydride → HCID 86733864, compound

HRID 2397915Notes

Reaction equation

HRID 2397915 reaction equation
Br.[NH:2]1[C@@H:11]2[C@@H:6]([CH2:7][C:8]3[CH:15]=[C:14]([OH:16])[CH:13]=[CH:12][C:9]=3[CH2:10]2)[CH2:5][CH2:4][CH2:3]1.O.O.O.[C:20]([O-:23])(=O)[CH3:21].[Na+].[C:25](OC(=O)C)(=[O:27])[CH3:26]>>[C:25]([N:2]1[C@@H:11]2[C@@H:6]([CH2:7][C:8]3[CH:15]=[C:14]([O:16][C:20](=[O:23])[CH3:21])[CH:13]=[CH:12][C:9]=3[CH2:10]2)[CH2:5][CH2:4][CH2:3]1)(=[O:27])[CH3:26]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 23665404Sodium Acetate TrihydrateHCID 86733865HCID 86733865, compound

Product 1

HCID 86733864HCID 86733864, compound

Procedure

A mixture of 1.4 g. of cis-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinolin-7-ol hydrobromide, 2.1 g. of sodium acetate trihydrate, and 14 ml. of acetic anhydride was stirred and heated on a steam bath for one hour. The solvent was evaporated from the mixture and the resulting residue was partitioned between water and diethyl ether. The ether layer was washed with saturated aqueous sodium bicarbonate solution, dried, and filtered, and the filtrate was evaporated. The residue thus obtained was crystallized from hexane to yield cis-1,2,3,4,4a,5,10,10a-octahydro-1-acetyl-7-acetoxybenzo[g]quinoline, m.p. 108°-113° C. The nmr spectrum (CDCl3) showed 3 aryl protons (400-430 Hz) and two methyl singlets (125, 133 Hz).

Workup

  1. additionA mixture of 1.4 g
  2. temperatureheated on a steam bath for one hour
  3. customThe solvent was evaporated from the mixture
  4. customthe resulting residue was partitioned between water and diethyl ether
  5. washThe ether layer was washed with saturated aqueous sodium bicarbonate solution
  6. customdried
  7. filtrationfiltered
  8. customthe filtrate was evaporated
  9. customThe residue thus obtained
  10. customwas crystallized from hexane

Sources & evidence

ORD record
ord-9c224b6e41c84fb5b879d3fb45f528c3
Source dataset
uspto-grants-1977_05
Patent number
US04022792

Reaction notes

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