Phosphorus oxychloride → HCID 86615001, compound

HRID 732409Notes

Reaction equation

HRID 732409 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9](OC)[N:8]=[C:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:6]=1)=[O:4].P(Cl)(Cl)([Cl:20])=O>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9]([Cl:20])[N:8]=[C:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 68814472HCID 68814472, compound

Product 1

HCID 86615001HCID 86615001, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

Mix 6-methoxypyridine-2,4-dicarboxylic acid 2-ethyl ester 4-methyl ester (239 mg, 1.0 mmol), phosphorous oxychloride (0.46 mL, 4.93 mmol) in DMF (1.9 mL) and heat to 85° C. for 24 h. Cool to room temperature and quench with saturated aqueous sodium acetate solution (5 mL). Extract with ethyl acetate, wash with water, dry (sodium sulfate), concentrate and purify (silica gel chromatography, eluting with ethyl acetate and hexanes) to give the title compound (190 mg, 78%).

Workup

  1. temperatureCool to room temperature
  2. customquench with saturated aqueous sodium acetate solution (5 mL)
  3. extractionExtract with ethyl acetate
  4. washwash with water
  5. dry with materialdry (sodium sulfate)
  6. concentrationconcentrate
  7. custompurify
  8. wash(silica gel chromatography, eluting with ethyl acetate and hexanes)

Sources & evidence

ORD record
ord-185e38d420374e58b3d77edb0918e979
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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