Lithium Hydroxide → 4-[(4,4-Dimethyl-2-heptylthio-3,4-dihydro-6-quinolinyl)ethynyl]benzoic acid

HRID 52443Notes

Reaction equation

HRID 52443 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]=[C:4]([S:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:3]1.[Li+].[OH-].CC1(C)C2C(=CC=C(C#CC3C=CC(C(O)=O)=CC=3)C=2)N=C(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]=[C:4]([S:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:3]1

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 199637054-[(4,4-Dimethyl-2-iso-propoxy-3,4-dihydro-6-quinolinyl)ethynyl]benzoic acid2×HCID 19963725Ethyl 4-[(4,4-dimethyl-2-heptylthio-3,4-dihydro-6-quinolinyl)ethynyl]benzoate2×

Product 1

HCID 199637084-[(4,4-Dimethyl-2-heptylthio-3,4-dihydro-6-quinolinyl)ethynyl]benzoic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.0647 g (0.140 mmol) of ethyl 4-[(4,4-dimethyl-2-heptylthio-3,4-dihydro-6-quinolinyl)ethynyl]benzoate (Compound 10) in 2 ml of THF, 1 ml of EtOH was reacted with 2 ml of 1N LiOH substantially in accordance with the procedure used for the preparation of 4-[(4,4-dimethyl-2-iso-propoxy-3,4-dihydro-6-quinolinyl)ethynyl]benzoic acid (Compound 11). Purification by recrystallization in acetonitrile yielded the title compound as a yellow powder.

Workup

  1. customPurification
  2. customby recrystallization in acetonitrile

Sources & evidence

ORD record
ord-bdfda93f015444d8a9e6d878058ffe32
Source dataset
uspto-grants-1997_04
Patent number
US05616712

Reaction notes

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