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Sodium Cyanide → 2-(2-Methylpyridin-3-yl)acetonitrile

HRID 889296
Notes
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Reaction equation

HRID 889296 reaction equation
Cl[CH2:2][C:3]1[C:4]([CH3:9])=[N:5][CH:6]=[CH:7][CH:8]=1.[C-:10]#[N:11].[Na+].[Cl-].[NH4+]>CN(C=O)C>[CH3:9][C:4]1[C:3]([CH2:2][C:10]#[N:11])=[CH:8][CH:7]=[CH:6][N:5]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 25517Ammonium ChlorideHCID 122437113-(Chloromethyl)-2-methylpyridine

Product 1

HCID 190992862-(2-Methylpyridin-3-yl)acetonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C
On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Procedure

970 mg (6.85 mmol) of the compound from Example 37A are initially introduced into 10 ml DMF, 336 mg (6.85 mmol) sodium cyanide are added and the mixture is stirred overnight at 45° C. The reaction mixture is introduced on to 75 ml saturated ammonium chloride solution and extracted several times with methylene chloride. The combined organic phases are dried over sodium sulfate, filtered and concentrated. The residue is purified by means of flash chromatography on silica gel (mobile phase: methylene chloride/methanol 20:1).

Workup

  1. additionare added
  2. extractionextracted several times with methylene chloride
  3. dry with materialThe combined organic phases are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is purified by means of flash chromatography on silica gel (mobile phase: methylene chloride/methanol 20:1)

Sources & evidence

ORD record
ord-3b8056ed72f54a7daab4e4e314dd8c78
Source dataset
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08252817B2

Reaction notes

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