Hydrochloric Acid → 2-Quinolinemethanol

HRID 742927Notes

Reaction equation

HRID 742927 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]=[O:12].[BH4-].[Na+].Cl>C(O)C>[OH:12][CH2:11][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 796192-QuinolinecarboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 731962-QuinolinemethanolYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3.0 g of quinoline-2-carboxaldehyde in 100 ml of ethanol was treated with 750 mg of sodium borohydride and stirred at ambient temperature for 15 min. The resulting solution was neutralized with 1N HCl, concentrated in vacuo, and extracted three times with ethyl acetate. The combined organic layers were dried over Na2SO4 and concentrated to provide 2.65 g (88%) of the crude desired compound.

Workup

  1. concentrationconcentrated in vacuo
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b6169bd1c6c7480f88b3f266eacc055f
Source dataset
uspto-grants-1996_09
Patent number
US05554783

Reaction notes

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