Potassium Hydroxide → 8-[p-(benzyloxy)phenyl]-7-oxo-7H-thieno[2,3-a]quinolizine-10-carboxylic acid

HRID 362554Notes

Reaction equation

HRID 362554 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16](=[O:32])[N:17]3[C:22](=[C:23]([C:25]([O:27]C)=[O:26])[CH:24]=2)[C:21]2[S:29][CH:30]=[CH:31][C:20]=2[CH:19]=[CH:18]3)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>C(O)C.O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[C:16](=[O:32])[N:17]3[C:22](=[C:23]([C:25]([OH:27])=[O:26])[CH:24]=2)[C:21]2[S:29][CH:30]=[CH:31][C:20]=2[CH:19]=[CH:18]3)=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 19353633methyl 8-[p-(benzyloxy)phenyl]-7-oxo-7H-thieno[2,3-a]quinolizine-10-carboxylate

Product 1

HCID 193536298-[p-(benzyloxy)phenyl]-7-oxo-7H-thieno[2,3-a]quinolizine-10-carboxylic acidYield 748.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

0.23 g (0.5 mmol) of methyl 8-[p-(benzyloxy)phenyl]-7-oxo-7H-thieno[2,3-a]-quinolizine-10-carboxylate in 2 ml of ethanol was stirred overnight under reflux with a solution of 0.06 g of potassium hydroxide in 1.25 ml of water. Acidification to pH 1 with 1N hydrochloric acid and removal of the precipitate by filtration yielded 1.6 g (72%) of 8-[p-(benzyloxy)phenyl]-7-oxo-7H-thieno[2,3-a]quinolizine-10-carboxylic acid with m.p. 197°-199° C.

Workup

  1. customAcidification to pH 1 with 1N hydrochloric acid and removal of the precipitate
  2. filtrationby filtration

Sources & evidence

ORD record
ord-df334377d60d4f2181abb4874e671dde
Source dataset
uspto-grants-1999_02
Patent number
US05869500

Reaction notes

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