Acetic Anhydride → 5,6,13,13a-tetrahydro-2,3,11-trimethoxy-10-acetoxy-8H-dibenzo [a,g]quinolizine

HRID 1580595Notes

Reaction equation

HRID 1580595 reaction equation
[OH:1][C:2]1[C:3]([O:24][CH3:25])=[CH:4][C:5]2[CH2:14][CH:13]3[N:8]([CH2:9][CH2:10][C:11]4[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[CH:15][C:12]=43)[CH2:7][C:6]=2[CH:23]=1.[C:26](OC(=O)C)(=[O:28])[CH3:27]>N1C=CC=CC=1>[CH3:22][O:21][C:16]1[C:17]([O:19][CH3:20])=[CH:18][C:11]2[CH2:10][CH2:9][N:8]3[CH:13]([CH2:14][C:5]4[CH:4]=[C:3]([O:24][CH3:25])[C:2]([O:1][C:26](=[O:28])[CH3:27])=[CH:23][C:6]=4[CH2:7]3)[C:12]=2[CH:15]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 1228511210-hydroxy-2,3,11-trimethoxy-5,6,13,13a-tetrahydro-8H-dibenzo[a, g]quinolizine

Product 1

HCID 117943615,6,13,13a-tetrahydro-2,3,11-trimethoxy-10-acetoxy-8H-dibenzo [a,g]quinolizineYield 33.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

0.8 g. of 10-hydroxy-2,3,11-trimethoxy-5,6,13,13a-tetrahydro-8H-dibenzo[a, g]quinolizine was dissolved in 8 ml of anhydrous pyridine. To the resulting solution 2 ml of acetic anhydride was added dropwise with stirring, while cooling in an ice-bath. After the mixture was stirred at room temperature for 5 hours, the excessive acetic anhydride was distilled off under reduced pressure, and the residue obtained was extracted with chloroform. The chloroform layer was washed with a 1N-sodium hydroxide solution and then with water, dried over potassium carbonate and evaporated to dryness. Recrystallization of the residue from ethanol-petroleum ether afforded 0.3 g. (33.3% yield) of 5,6,13,13a-tetrahydro-2,3,11-trimethoxy-10-acetoxy-8H-dibenzo [a,g]quinolizine as colorless needles having a melting point of 162° to 164°C.

Workup

  1. temperaturewhile cooling in an ice-bath
  2. stirringAfter the mixture was stirred at room temperature for 5 hours
  3. distillationthe excessive acetic anhydride was distilled off under reduced pressure
  4. customthe residue obtained
  5. extractionwas extracted with chloroform
  6. washThe chloroform layer was washed with a 1N-sodium hydroxide solution
  7. dry with materialwith water, dried over potassium carbonate
  8. customevaporated to dryness
  9. customRecrystallization of the residue from ethanol-petroleum ether
  10. customafforded 0.3 g

Sources & evidence

ORD record
ord-8755c4d770f447a7b869754ad8017eb6
Source dataset
uspto-grants-1976_01
Patent number
US03933826

Reaction notes

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