Sodium borohydride → (5-Bromoquinolin-8-yl)methanol

HRID 1849997Notes

Reaction equation

HRID 1849997 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]([CH:12]=[O:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[BH4-].[Na+]>CO.C1COCC1>[Br:1][C:2]1[CH:11]=[CH:10][C:9]([CH2:12][OH:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 164142435-Bromoquinoline-8-carboxaldehyde

Product 1

HCID 72183353(5-Bromoquinolin-8-yl)methanolYield 100.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-bromoquinoline-8-carbaldehyde ([CAS 885267-41-7] 423 mg, 1.79 mmol) in MeOH (5 mL) and THF (10 mL) was added sodium borohydride (68 mg, 1.79 mmol) at 0° C. After stirring at 0° C. for 30 min, the reaction mixture was quenched with a saturated aqueous ammonium chloride solution. The mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried with magnesium sulfate and concentrated under reduced pressure to give rise to 430 mg of the title compound as a yellow solid.

Workup

  1. customthe reaction mixture was quenched with a saturated aqueous ammonium chloride solution
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e0417a9ab70e4cf1a15f473ae666edb6
Source dataset
uspto-grants-2015_02
Patent number
US08957051B2

Reaction notes

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