Hydrochloric Acid → (Quinolin-3-yl)methanol

HRID 1271775Notes

Reaction equation

HRID 1271775 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH:11]=[O:12])[CH:2]=1.[BH4-].[Na+].Cl.[OH-].[Na+]>CCO>[OH:12][CH2:11][C:3]1[CH:2]=[N:1][C:10]2[C:5]([CH:4]=1)=[CH:6][CH:7]=[CH:8][CH:9]=2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 836413-QuinolinecarboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 12662983(Quinolin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Quinoline 3-carboxaldehyde (1.0 g, 6.37 mmol) was dissolved in 20 mL of EtOH and treated with NaBH4 (70 mg). After stirring for 1 hour, the solution was treated with 2 mL of 1N HCl, and after stirring for 10 min the reaction mixture was treated with enough 1N NaOH to make the solution basic. The reaction temperature was extracted with Et2O and the organic portion was washed with H2O and brine. The organic portion was dried over Na2SO4 and concentrated under reduced pressur to give the title compound. MS(CI) m/e 160 (M+H)+.

Workup

  1. stirringafter stirring for 10 min the reaction mixture
  2. extractionThe reaction temperature was extracted with Et2O
  3. washthe organic portion was washed with H2O and brine
  4. dry with materialThe organic portion was dried over Na2SO4
  5. concentrationconcentrated under reduced pressur

Sources & evidence

ORD record
ord-a40e816a12f7424799d2502e1293296a
Source dataset
uspto-grants-2007_04
Patent number
USRE039591E1

Reaction notes

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