Ammonium Chloride → 5-(Hydroxymethyl)nicotinonitrile

HRID 45238Notes

Reaction equation

HRID 45238 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:8][OH:9])[CH:5]=[N:6][CH:7]=1.[Cu](C#N)[C:11]#[N:12].[NH4+].[Cl-]>N1C=CC=CC=1.N>[OH:9][CH2:8][C:4]1[CH:3]=[C:2]([C:11]#[N:12])[CH:7]=[N:6][CH:5]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 2784733(5-Bromo-3-pyridinyl)methanolHCID 178418260HCID 178418260, compound

Product 1

HCID 224165405-(Hydroxymethyl)nicotinonitrileYield 71.1%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 1049PyridineSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 4.2 g (22.34 mmol) of (5-bromopyridin-3-yl)methanol and 5 g (55.84 mmol) of copper cyanide in 22 mL of pyridine is heated for 20 hours in a sealed tube at 160° C. After cooling to room temperature, the medium is taken up in 10 mL of concentrated aqueous ammonia and 30 mL of saturated NH4Cl solution and then stirred for 2 hours. The medium is then extracted with 200 mL of a DCM/iPrOH mixture (85/15), dried over Na2SO4 and then concentrated under reduced pressure and purified by chromatography on a column of silica gel, eluting with a 98/2 DCM/MeOH mixture. 2.13 g of 5-(hydroxymethyl)pyridine-3-carbonitrile are obtained in the form of a white solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionThe medium is then extracted with 200 mL of a DCM/iPrOH mixture (85/15)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. custompurified by chromatography on a column of silica gel
  6. washeluting with a 98/2 DCM/MeOH mixture

Sources & evidence

ORD record
ord-e2beaf72d4444e209b36f2cd86514448
Source dataset
uspto-grants-2013_09
Patent number
US08541455B2

Reaction notes

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