Lithium hydroxide, monohydrate → HCID 67134061, compound
Reaction equation
O.[OH-].[Li+].C([O:6][C:7]([C:9]1[C:10]([S:24][CH2:25][CH3:26])=[N:11][C:12]2[C:17]([C:18]=1[CH3:19])=[CH:16][CH:15]=[C:14]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:13]=2)=[O:8])C.C1COCC1.CO>O>[C:20]([C:14]1[CH:13]=[C:12]2[C:17]([C:18]([CH3:19])=[C:9]([C:7]([OH:8])=[O:6])[C:10]([S:24][CH2:25][CH3:26])=[N:11]2)=[CH:16][CH:15]=1)([CH3:23])([CH3:21])[CH3:22]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A solution of 600 mg (14.36 mmol) lithium hydroxide monohydrate in water (30 ml) was added to a solution of 1.7 g (5.1 mmol) 7-tert-butyl-2-ethylsulfanyl-4-methyl-quinoline-3-carboxylic acid ethyl ester in a THF/methanol blend (2:1 vv, 30 ml) and then the reaction solution was stirred for 16 h at 60° C. Then the mixture was concentrated to small volume under vacuum and the residue was taken up with water and washed with EE. The aqueous phase was adjusted to pH 2 with 1M hydrochloric acid and then extracted with EE. The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated to small volume under vacuum. 420 mg (1.38 mmol, 27%) 7-tert-butyl-2-ethylsulfanyl-4-methyl-quinoline-3-carboxylic acid were obtained as the residue, which was reacted further with no additional purification.
Workup
- concentrationThen the mixture was concentrated to small volume under vacuum
- washwashed with EE
- extractionextracted with EE
- washThe organic phase was washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated to small volume under vacuum
Sources & evidence
- ORD record
- ord-43c1508c87ce4f1c8cfd68627e00b854
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08399673B2
Reaction notes
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