Sodium Cyanide → 6-(Hydroxymethyl)pyridine-3-carbonitrile

HRID 643282Notes

Reaction equation

HRID 643282 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([CH2:8][OH:9])=[N:6][CH:7]=1.[C-:10]#[N:11].[Na+]>C(C#N)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[C:10]([C:2]1[CH:3]=[CH:4][C:5]([CH2:8][OH:9])=[N:6][CH:7]=1)#[N:11]

Participants

6

Reactant 2

HCID 8929Sodium CyanideHCID 5200169(5-Bromopyridin-2-yl)methanol

Product 1

HCID 534276876-(Hydroxymethyl)pyridine-3-carbonitrileYield 48%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 7854PropionitrileSolvent

Conditions

Temperature
110 °C

Procedure

(5-Bromo-pyridin-2-yl)-methanol (1.0 g), NaCN (521 mg), Pd(PPh3)4 (612 mg), and CuI (200 mg) were taken up in degassed EtCN and heated at 110° C. (4 h). The solution was partitioned between EtOAc and 10% NH4OH(aq.). The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine and dried (MgSO4). Filtration and concentration gave a yellow solid. Purification via flash chromatography (1/2 hexanes/EtOAc, SiO2) gave 341 mg (48%) of (5-cyano-pyridin-2-yl)-methanol as a white solid.

Workup

  1. customThe solution was partitioned between EtOAc and 10% NH4OH(aq.)
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationFiltration and concentration
  6. customgave a yellow solid
  7. customPurification via flash chromatography (1/2 hexanes/EtOAc, SiO2)

Sources & evidence

ORD record
ord-5a42732d066640369b4b23029fea2976
Source dataset
uspto-grants-2010_04
Patent number
US07700597B2

Reaction notes

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