Thionyl Chloride → 5-(Chloromethyl)pyridine-3-carbonitrile

HRID 736995Notes

Reaction equation

HRID 736995 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][C:7]1[CH:8]=[N:9][CH:10]=[C:11]([CH:14]=1)[C:12]#[N:13].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:3][CH2:6][C:7]1[CH:8]=[N:9][CH:10]=[C:11]([CH:14]=1)[C:12]#[N:13]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 224165405-(Hydroxymethyl)nicotinonitrile

Product 1

HCID 221467115-(Chloromethyl)pyridine-3-carbonitrileYield 9.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add thionyl chloride (1 mL) to a solution of 5-hydroxymethyl-nicotinonitrile (45 mg, 0.34 mmol, 1 equiv) in anhydr CH2Cl2 (1 mL). After 20 min, basify the reaction with satd aq NaHCO3 (12 mL). Extract this mixture with Et2O (2×5 mL). Dry the combined organic layers (anhydr MgSO4) and rotary evaporate (40° C.) to yield 4.9 mg (9.6%) of 5-chloromethyl-nicotinonitrile as a yellow film. MS (m/z): 152.

Workup

  1. extractionExtract this mixture with Et2O (2×5 mL)
  2. dry with materialDry the combined organic layers (anhydr MgSO4)
  3. customrotary evaporate (40° C.)

Sources & evidence

ORD record
ord-8c5a1eb4cac846adac27b39f2136c211
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

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