Hydrochloric Acid → 2-Quinolinemethanol

HRID 1737100Notes

Reaction equation

HRID 1737100 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-685a7896143c4fd88563233eb5c09c42
Source dataset
uspto-grants-1996_07
Patent number
US05541334

Reaction notes

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