Methanol → Quinolin-8-ylmethanol

HRID 2177012Notes

Reaction equation

HRID 2177012 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](C=O)[CH:4]=1.[CH3:15][OH:16]>>[N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[CH2:15][OH:16])[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 836413-QuinolinecarboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 594412Quinolin-8-ylmethanolYield 75%

Procedure

Sodium borohydride (280 mg, 7.4 mmol) was added in portions to a solution of 3-quinoline-carboxaldehyde (1.06 g, 6.7 mmol) in methanol at room temperature. Reaction was quenched after 3 hours stirring with 10 mL (aq) sat. NH4Cl. Mixture was extracted with ethyl acetate (3×30 ml). Combined organics were washed with brine and dried over MgSO4. Crude material was purified by chromatography using (20-40% EA/Hex gradient) to afford quinolin-8-yl-methanol as an off white solid (800 mg; 75% 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
  6. customCrude material was purified by chromatography

Sources & evidence

ORD record
ord-c75c42d96c7240fc8f6aa8aa5994c72d
Source dataset
uspto-grants-2015_06
Patent number
US09067897B2

Reaction notes

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