Pyridine → HCID 22141268, compound

HRID 1826484Notes

Reaction equation

HRID 1826484 reaction equation
O[CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=1)[C:3]#[N:4].N1C=CC=CC=1.S(Cl)([Cl:22])=O>C(OCC)C>[Cl:22][CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=1)[C:3]#[N:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 32778082-Hydroxy-2-(3-nitrophenyl)acetonitrile

Product 1

HCID 22141268HCID 22141268, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 2-hydroxy-2-(3-nitrophenyl)acetonitrile (Preparation 113, 1.0 g, 5.62 mmol) in diethyl ether (10 ml) was stirred at room temperature and treated with pyridine (0.1 ml, 1.24 mmol) followed by thionyl chloride (0.82 ml, 11.2 mmol) dropwise over 5 minutes. The mixture was gently heated under reflux and after 30 min the solvent was removed by evaporation to give a pale yellow solid. This was purified by column chromatography on silica gel eluting with hexane:ethyl acetate (3:1 and then 2:1) to give the title compound as a white crystalline solid (980 mg, 89%).

Workup

  1. temperatureThe mixture was gently heated
  2. temperatureunder reflux and after 30 min the solvent
  3. customwas removed by evaporation
  4. customto give a pale yellow solid
  5. customThis was purified by column chromatography on silica gel eluting with hexane:ethyl acetate (3:1

Sources & evidence

ORD record
ord-7c0a6bca5b5b4ced8c0ae0fd1dd0403a
Source dataset
uspto-grants-2006_05
Patent number
US07049444B2

Reaction notes

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