Acetic Acid → 4-(Hydroxymethyl)quinoline

HRID 1164853Notes

Reaction equation

HRID 1164853 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH:11]=[O:12])=[CH:3][CH:2]=1.[BH4-].[Na+].O.C(O)(=O)C>C(O)C>[OH:12][CH2:11][C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]=[CH:2][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 780724-QuinolinecarboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 804794-(Hydroxymethyl)quinoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 10 g of 4-quinolinecarboxaldehyde in 400 ml of absolute ethanol at room temperature is added 2.4 g of sodium borohydride. After 45 minutes, 20 ml of water is added and the reaction mixture is stirred for an additional 20 minutes. Acetic acid (20 ml) is added slowly. The reaction mixture is evaporated to a small volume and partitioned between water and methylene chloride. The organic layer is washed with saturated potassium carbonate, saturated sodium chloride solution, dried over sodium sulfate and evaporated to dryness. The residue is purified by chromatography on silica gel using methanol/methylene chloride (1:10) as eluent to yield 4-hydroxymethylquinoline; Rf =0.59.

Workup

  1. customThe reaction mixture is evaporated to a small volume
  2. custompartitioned between water and methylene chloride
  3. washThe organic layer is washed with saturated potassium carbonate, saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness
  6. customThe residue is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-5e145125e6054b59aa8f8f5213a79553
Source dataset
uspto-grants-1990_03
Patent number
US04906621

Reaction notes

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