Hydrochloric Acid → HCID 14372189, compound

HRID 1382904Notes

Reaction equation

HRID 1382904 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10](/[C:14](/[CH3:26])=[CH:15]/[C:16]3[CH:25]=[CH:24][C:19]([C:20]([O:22]C)=[O:21])=[CH:18][CH:17]=3)=[CH:11][CH:12]=2)[C:7]([CH3:28])([CH3:27])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[OH-].[Na+].Cl>O1CCOCC1.O>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10](/[C:14](/[CH3:26])=[CH:15]/[C:16]3[CH:17]=[CH:18][C:19]([C:20]([OH:22])=[O:21])=[CH:24][CH:25]=3)=[CH:11][CH:12]=2)[C:7]([CH3:28])([CH3:27])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 14372188HCID 14372188, compound

Product 1

HCID 14372189HCID 14372189, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 0.1 g (0.265 mmol) of methyl 4[(E)-2-(N-acetyl-4,4-dimethyl-1,2,3,4-tetrahydro-6-quinolinyl)-2-methylvinyl]benzoate in 10 ml of dioxane was added, with stirring, 0.8 ml (1.6 mmol) of 2N sodium hydroxide, with the temperature maintained at 25° C. Stirring was continued for 48 hours, and then the reaction mixture was diluted with 25 ml of water. It was then acidified to pH 2 with 2N hydrochloric acid and extracted with dichloromethane. The combined extracts were dried using sodium sulfate and then evaporated in vacuo to give the title compound as a white solid. The solid was recrystallized from methanol-hexane to give 70 mg of the title compound, mp 200°-202° C.

Workup

  1. stirringStirring
  2. extractionextracted with dichloromethane
  3. customThe combined extracts were dried
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-7993abd36d824ce18781b59e21cd0963
Source dataset
uspto-grants-1989_02
Patent number
US04808597

Reaction notes

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