Sodium borohydride → HCID 11668580, compound

HRID 1712066Notes

Reaction equation

HRID 1712066 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]=[C:20]([CH:22]=[O:23])[CH:19]=[CH:18][C:17]=1[O:24][CH3:25])=[CH:13][CH:12]=[C:11]([C:26]([F:29])([F:28])[F:27])[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]=[C:20]([CH2:22][OH:23])[CH:19]=[CH:18][C:17]=1[O:24][CH3:25])=[CH:13][CH:12]=[C:11]([C:26]([F:29])([F:27])[F:28])[CH:10]=2)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 11603785HCID 11603785, compound

Product 1

HCID 11668580HCID 11668580, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(5-Formyl-2-methoxy-phenyl)-7-trifluoromethyl-quinoline-3-carboxylic acid ethyl ester (30 mg, 0.074 mmol) was dissolved in ethanol (1 mL) and treated with sodium borohydride (26 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 was dried over sodium sulfate, concentrated. The crude compound was purified by column chromatography eluted with 30% ethyl acetate to yield 4-(5-hydroxymethyl-2-methoxy-phenyl)-7-trifluoromethyl-quinoline-3-carboxylic acid ethyl ester as a white solid.

Workup

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

Sources & evidence

ORD record
ord-e89532d587a84b43968ebe1802edab2c
Source dataset
uspto-grants-2010_09
Patent number
US07790895B2

Reaction notes

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