Acetic Acid → HCID 13961482, compound

HRID 2309668Notes

Reaction equation

HRID 2309668 reaction equation
[N:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[C:3]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:2]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17].[C:21]([OH:24])(=[O:23])[CH3:22].OO.C(OC(=O)C)(=O)C>O>[C:21]([O:24][CH:9]1[C:10]2[N:1]=[C:2]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:3]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][C:5]=2[CH2:6][CH2:7][CH2:8]1)(=[O:23])[CH3:22]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen Peroxide2×HCID 7918Acetic AnhydrideHCID 13961481HCID 13961481, compound

Product 1

HCID 13961482HCID 13961482, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

A mixture comprising 2.8 g of diethyl 5,6,7,8-tetrahydroquinoline-2,3-dicarboxylate, 10 ml of acetic acid and 1.1 ml of a 35% hydrogen peroxide aqueous solution, was stirred at 75° C. for 3 hours under heating. 1.0 ml of a 35% hydrogen peroxide aqueous solution was added thereto, and the mixture was further reacted at 75° C. for 9 hours. After cooling the mixture, water was added thereto, and the mixture was extracted with chloroform. The organic layer was dried, and then the solvent was distilled off to obtain an oily substance. This oily substance was added to 50 ml of acetic anhydride under reflux, and refluxed for 15 minutes. The solvent was distilled off under reduced pressure. Water was added to the residue, and the mixture was extracted with diethyl ether. The organic layer was dried, and then the solvent was distilled off. The residue was purified by column chromatography to obtain 2.3 g (yield: 69%) of diethyl 8-acetoxy-5,6,7,8-tetrahydroquinoline-2,3-dicarboxylate.

Workup

  1. temperatureunder heating
  2. customthe mixture was further reacted at 75° C. for 9 hours
  3. additionwas added
  4. extractionthe mixture was extracted with chloroform
  5. customThe organic layer was dried
  6. distillationthe solvent was distilled off
  7. customto obtain an oily substance
  8. temperatureunder reflux
  9. temperaturerefluxed for 15 minutes
  10. distillationThe solvent was distilled off under reduced pressure
  11. additionWater was added to the residue
  12. extractionthe mixture was extracted with diethyl ether
  13. customThe organic layer was dried
  14. distillationthe solvent was distilled off
  15. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-7df910ac8f62474f90ef67f793a2458c
Source dataset
uspto-grants-1987_09
Patent number
US04696694

Reaction notes

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