Ethyl 4-[(4,4-dimethyl-2-methylthio-3,4-dihydro-6-quinolinyl)ethynyl]benzoate → 4-[(4,4-Dimethyl-2-methylthio-3,4-dihydro-6-quinolinyl)ethynyl]benzoic acid

HRID 52442Notes

Reaction equation

HRID 52442 reaction equation
[CH3:1][C:2]1([CH3:27])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[C:13][C:14]3[CH:24]=[CH:23][C:17]([C:18]([O:20]CC)=[O:19])=[CH:16][CH:15]=3)[CH:10]=2)[N:5]=[C:4]([S:25][CH3:26])[CH2:3]1>C1COCC1.CCO.[Li+].[OH-]>[CH3:1][C:2]1([CH3:27])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[C:13][C:14]3[CH:15]=[CH:16][C:17]([C:18]([OH:20])=[O:19])=[CH:23][CH:24]=3)[CH:10]=2)[N:5]=[C:4]([S:25][CH3:26])[CH2:3]1

Participants

5

Reactant 1

HCID 19963703Ethyl 4-[(4,4-dimethyl-2-methylthio-3,4-dihydro-6-quinolinyl)ethynyl]benzoate2×

Product 1

HCID 199637314-[(4,4-Dimethyl-2-methylthio-3,4-dihydro-6-quinolinyl)ethynyl]benzoic acid

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3939Lithium HydroxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.100 g (0.30 mmol) of ethyl 4-[(4,4-dimethyl-2-methylthio-3,4-dihydro-6-quinolinyl)ethynyl]benzoate (Compound 9) in 2 ml of THF, 1 ml of EtOH and 2 ml of 1N LiOH was stirred at room temperature for 1 h, followed by aqueous work up to yield the title compound as a yellow solid.

Sources & evidence

ORD record
ord-6d7e8b1ba72f411199edb6ae384d2761
Source dataset
uspto-grants-1997_04
Patent number
US05616712

Reaction notes

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