Sodium borohydride → HCID 59205225, compound

HRID 1712067Notes

Reaction equation

HRID 1712067 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH:22]=[O:23])[CH:17]=1)=[CH:13][CH:12]=[C:11]([C:24]([F:27])([F:26])[F:25])[CH:10]=2)=[O:5])[CH3:2].[BH4-].[Na+]>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][OH:23])[CH:17]=1)=[CH:13][CH:12]=[C:11]([C:24]([F:27])([F:25])[F:26])[CH:10]=2)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59205195HCID 59205195, compound

Product 1

HCID 59205225HCID 59205225, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(3-Formyl-phenyl)-7-trifluoromethyl-quinoline-3-carboxylic acid ethyl ester (16 mg, 0.034 mmol) was dissolved in ethanol (1 mL) and treated with sodium borohydride (15 mg) in one portion. After stirring at room temperature for 15 min the reaction mixture was quenched with an aqueous solution of ammonium chloride. The reaction mixture was then extracted with ethyl acetate and the organic layer dried over sodium sulfate, concentrated and the residue purified by to column chromatography eluted with 30% ethyl acetate to yield 4-(3-hydroxymethyl-phenyl)-7-trifluoromethyl-quinoline-3-carboxylic acid ethyl ester as a yellow solid.

Workup

  1. customwas quenched with an aqueous solution of ammonium chloride
  2. extractionThe reaction mixture was then extracted with ethyl acetate
  3. dry with materialthe organic layer dried over sodium sulfate
  4. concentrationconcentrated
  5. customthe residue purified by to column chromatography
  6. washeluted with 30% ethyl acetate

Sources & evidence

ORD record
ord-26085792d7e14c5cacfe31080d2858e8
Source dataset
uspto-grants-2010_09
Patent number
US07790895B2

Reaction notes

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