Water → HCID 19045350, compound

HRID 1466047Notes

Reaction equation

HRID 1466047 reaction equation
[BH4-].[Na+].[O:3]=[CH:4][CH2:5][C:6]1[N:11]=[CH:10][C:9]([C:12]#[N:13])=[CH:8][CH:7]=1.O>CO>[OH:3][CH2:4][CH2:5][C:6]1[N:11]=[CH:10][C:9]([C:12]#[N:13])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 895250136-(2-Oxoethyl)nicotinonitrile

Product 1

HCID 19045350HCID 19045350, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaBH4 (2.5 g, 67 mmol) was added in small portions to a solution of 6-(2-oxoethyl)pyridine-3-carbonitrile (5.0 g, crude) in 80 mL of MeOH at 0° C. The mixture was stirred at room temperature for 30 minutes and poured to 50 mL of water. The mixture was extracted with EtOAc (100 mL×5) and the combined organic layer was condensed. The residue was purified by flash chromatography to afford 6-(2-hydroxyethyl)pyridine-3-carbonitrile. TEA (2.1 g, 21 mmol) was added drop wise to a solution of 6-(2-hydroxyethyl)pyridine-3-carbonitrile (3.0 g, 20 mmol) and MsCl (2.3 g, 20 mmol) in 200 mL of DCM at 0° C. The mixture was stirred at RT for 30 minutes and washed with water and brine, dried over anhydrous Na2SO4 and condensed under vacuum below 30° C. to afford the title compound which was used immediately without further purification.

Workup

  1. extractionThe mixture was extracted with EtOAc (100 mL×5)
  2. customcondensed
  3. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-118a8191afc3495fb643a990d59505d2
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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