Sodium borohydride → 2-Cyano-5-hydroxymethylpyridine

HRID 1486657Notes

Reaction equation

HRID 1486657 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]#[N:10])=[N:7][CH:8]=1)=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][C:3]1[CH:4]=[CH:5][C:6]([C:9]#[N:10])=[N:7][CH:8]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 109862635-Formylpyridine-2-carbonitrile

Product 1

HCID 122519662-Cyano-5-hydroxymethylpyridineYield 86.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 5-formylpicolinonitrile (490 mg, 3.71 mmol) in 15 mL of MeOH was added NaBH4 (140 mg, 3.71 mmol). The reaction mixture was stirred at 0° C. for 1 h and quenched with 5% citric acid. After most MeOH was removed by concentration, the residue was partitioned between DCM and sat. NaHCO3 (aq.). The aqueous layer was extracted with DCM (10×). The organic layer was washed with brine and dried (Na2SO4). The product 5-(hydroxymethyl)picolinonitrile (431 mg) was obtained by concentration under vacuum.

Workup

  1. customquenched with 5% citric acid
  2. customAfter most MeOH was removed by concentration
  3. customthe residue was partitioned between DCM and sat. NaHCO3 (aq.)
  4. extractionThe aqueous layer was extracted with DCM (10×)
  5. washThe organic layer was washed with brine
  6. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-82534f88052c46c8a37ee823926d6ad5
Source dataset
uspto-grants-2016_08
Patent number
US09428475B2

Reaction notes

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