3-Quinolinecarboxaldehyde → (Quinolin-3-yl)methanol

HRID 1364432Notes

Reaction equation

HRID 1364432 reaction equation
[BH4-].[Na+].[N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[C:5]([CH:13]=[O:14])[CH:4]=1>CO>[N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[C:5]([CH2:13][OH:14])[CH:4]=1

Participants

4

Reactant 2

HCID 836413-QuinolinecarboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 12662983(Quinolin-3-yl)methanolYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (240 mg, 6.4 mmol) was added in portions to a solution of 3-Quinoline-carboxaldehyde (910 mg, 5.8 mmol) in methanol at room temperature. Reaction was quenched after 3 hours stirring with 10 mls (aq) sat. NH4Cl. Mixture was extracted with ethyl acetate (3×30 ml). Combined organics were washed with brine and dried over MgSO4. Crude Quinolin-3-ylmethanol was obtained upon filtration and concentration (795 mg; 86% yield).

Workup

  1. customReaction
  2. customwas quenched after 3 hours
  3. extractionMixture was extracted with ethyl acetate (3×30 ml)
  4. washCombined organics were washed with brine
  5. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-0e6ca74f431545cf9d27624309e880a1
Source dataset
uspto-grants-2011_02
Patent number
US07888366B2

Reaction notes

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