Potassium Sodium Tartrate → HCID 21891951, compound
Reaction equation
[Cl:1][C:2]1[C:11]([C:12](OCC)=[O:13])=[C:10]([CH2:17][CH3:18])[C:9]2[C:4](=[CH:5][C:6]([F:21])=[C:7]([O:19][CH3:20])[CH:8]=2)[N:3]=1.[H-].C([Al+]CC(C)C)C(C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>ClCCl>[Cl:1][C:2]1[C:11]([CH2:12][OH:13])=[C:10]([CH2:17][CH3:18])[C:9]2[C:4](=[CH:5][C:6]([F:21])=[C:7]([O:19][CH3:20])[CH:8]=2)[N:3]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
A solution of ethyl 2-chloro-4-ethyl-7-fluoro-6-methoxy-3-quinolinecarboxylate (10.8 g, 35 mmol) in anhydrous dichloromethane (200 ml) is treated dropwise at ambient temperature under an inert atmosphere with diisobutylaluminium hydride (1M in dichloromethane, 65 ml, 65 mmol), then heated at 40° C. for 4 hours. After cooling down to 0° C., a 20% aqueous solution of Rochelle salt (105 ml) and dichloromethane (200 ml) are added cautiously and the reaction mixture is maintained under agitation for 1 hour, followed by decanting and washing three times with water. The organic phase is dried over magnesium sulphate and the solvent is evaporated off. The residue is purified by column chromatography (SiO2, AcOEt/Hpt: 5/95 to 50/50). 6 g of a white solid is obtained.
Workup
- temperatureAfter cooling down to 0° C.
- temperaturethe reaction mixture is maintained under agitation for 1 hour
- customby decanting
- washwashing three times with water
- dry with materialThe organic phase is dried over magnesium sulphate
- customthe solvent is evaporated off
- customThe residue is purified by column chromatography (SiO2, AcOEt/Hpt: 5/95 to 50/50)
Sources & evidence
- ORD record
- ord-2521da5500264eba9453a64b6e595e67
- Source dataset
- uspto-grants-2006_11
- Patent number
- US07135478B2
Reaction notes
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