Sodium borohydride → 3-(2-Hydroxyethyl)isonicotinonitrile

HRID 1844014Notes

Reaction equation

HRID 1844014 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[CH2:9][C:10](OCC)=[O:11])#[N:2].[BH4-].[Na+]>C(O)C>[OH:11][CH2:10][CH2:9][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:3]=1[C:1]#[N:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 12251980Ethyl 2-(4-cyanopyridin-3-YL)acetate

Product 1

HCID 899647553-(2-Hydroxyethyl)isonicotinonitrileYield 36.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 2-(4-cyanopyridin-3-yl)acetate (2.3 g, 12.10 mmol) was reacted with NaBH4 (919 mg, 24.21 mmol) and ethanol (20 mL) at room temperature for 72 hours to afford the crude product. Purification by column chromatography on silica gel (2% methanol in CHCl3) afforded 650 mg of the product.

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (2% methanol in CHCl3)

Sources & evidence

ORD record
ord-fdf4b935e06142aaba6872f4e4a0be10
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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