Lithium Hydroxide → 4-[(4,4-Dimethyl-2-oxo-1,2,3,4-tetrahydro-1-benzyl-6-quinolinyl)ethynyl]benzoic acid

HRID 52456Notes

Reaction equation

HRID 52456 reaction equation
[CH3:1][C:2]1([CH3:33])[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]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:4](=[O:32])[CH2:3]1.[Li+].[OH-].CC1(C)C2C(=CC=C(C#CC3C=CC(C(O)=O)=CC=3)C=2)NC(OC(C)C)C1>C1COCC1.CCO>[CH3:1][C:2]1([CH3:33])[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]([CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:4](=[O:32])[CH2:3]1

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 19963704Ethyl 4-[(4,4-dimethyl-2-oxo-1,2,3,4-tetrahydro-1-benzyl-6-quinolinyl)ethynyl]benzoate2×HCID 539580744-[4,4-Dimethyl-2-isopropoxy-1,2,3,4-tetrahydro-6-quinolinyl]ethynyl benzoic acid2×

Product 1

HCID 199637334-[(4,4-Dimethyl-2-oxo-1,2,3,4-tetrahydro-1-benzyl-6-quinolinyl)ethynyl]benzoic acidYield 139.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

95.6 mg (0.23 mmol) of ethyl 4-[(4,4-dimethyl-2-oxo-1,2,3,4-tetrahydro-1-benzyl-6-quinolinyl)ethynyl]benzoate (Compound 37) in 2 ml of THF, 2 ml of EtOH, and 1 ml of 1N LiOH were reacted substantially in accordance with the procedure used for the preparation of 4-[4,4-dimethyl-2-isopropoxy-1,2,3,4-tetrahydro-6-quinolinyl]ethynyl benzoic acid (Compound 11) to give the title compound as a white solid (131 mg).

Sources & evidence

ORD record
ord-1e4093ac78cb49dabcd05162c0c3d451
Source dataset
uspto-grants-1997_04
Patent number
US05616712

Reaction notes

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