Phosphorus oxychloride → HCID 19832724, compound

HRID 2051124Notes

Reaction equation

HRID 2051124 reaction equation
O[C:2]1[C:3]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][N:5]2[CH:10]=1.P(Cl)(Cl)([Cl:18])=O>C(#N)C>[Cl:18][C:2]1[C:3]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][N:5]2[CH:10]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 17913309HCID 17913309, compound

Product 1

HCID 19832724HCID 19832724, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3.0 g of ethyl 2-hydroxypyrrolo [1,2-a]pyridine-1-carboxylate in 50 ml of acetonitrile, 2.7 g of phosphorus oxychloride is added at room temperature and stirred for 2 hours. The reaction mixture is concentrated under reduced pressure, added with water and then extracted with dichloromethane. The extract is dried on anhydrous sodium sulfate and distilled to remove dichloromethane. The residue is purified by silica gel chromatography (eluent: n-hexane-ethyl acetate) to give 2.0 g of the title compound as crystals.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. additionadded with water
  3. extractionextracted with dichloromethane
  4. dry with materialThe extract is dried on anhydrous sodium sulfate
  5. distillationdistilled
  6. customto remove dichloromethane
  7. customThe residue is purified by silica gel chromatography (eluent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-d2bb1a7610014bce86771faf4a31af18
Source dataset
uspto-grants-1991_05
Patent number
US05017212

Reaction notes

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