3-Quinolinecarboxaldehyde → (Quinolin-3-yl)methanol

HRID 576957

Reaction equation

HRID 576957 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+]>C(O)C>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH2:11][OH:12])[CH:2]=1

Participants

4

Reactant 2

HCID 836413-QuinolinecarboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 12662983(Quinolin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

In a 250 mL round bottom flask, quinoline-3-carbaldehyde (1.57 g, 10 mmol) was dissolved anhydrous ethanol (20 mL). The solution was cooled to 0° C. under nitrogen. NaBH4 (420 mg, 11 mmol) was added in one portion. The mixture was stirred at room temperature for 2 hours, and quenched by addition of water (3 mL). Na2SO4 (15 g) was added. After 10 minutes, the mixture was filtered. The filtrate was evaporated to provide quinolin-3-ylmethanol.

Workup

  1. customquenched by addition of water (3 mL)
  2. additionNa2SO4 (15 g) was added
  3. waitAfter 10 minutes
  4. filtrationthe mixture was filtered
  5. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-5cb8498e4d874eee874d8ceafcc87088
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Linked notes

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