Pyridine → HCID 22141268, compound

HRID 428972Notes

Reaction equation

HRID 428972 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-f1ca5067dba844f2bb60468c4c87d628
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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