Phosphorus oxychloride → Dimethyl 4-chloropyridine-3,5-dicarboxylate

HRID 59953Notes

Reaction equation

HRID 59953 reaction equation
O=[C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][NH:5][CH:4]=[C:3]1[C:12]([O:14][CH3:15])=[O:13].O=P(Cl)(Cl)[Cl:18]>>[Cl:18][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][N:5]=[CH:4][C:3]=1[C:12]([O:14][CH3:15])=[O:13]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 113901994-Oxo-1,4-dihydro-pyridine-3,5-dicarboxylic acid dimethyl ester

Product 1

HCID 22019198Dimethyl 4-chloropyridine-3,5-dicarboxylateYield 33.7%

Conditions

Temperature
140 °C

Procedure

A mixture of dimethyl 4-oxo-1,4-dihydropyridine-3,5-dicarboxylate (3 g, crude) and POCl3 (10 mL) was heated to 140° C. in the sealed tube for 15 hours. The mixture was cooled to RT, poured into ice and extracted with ether. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to afford the title compound as solid (yield 33.7%).

Workup

  1. temperatureThe mixture was cooled to RT
  2. additionpoured into ice
  3. extractionextracted with ether
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d14a058bf7e8446199a5ef4d0ec86e68
Source dataset
uspto-grants-2016_09
Patent number
US09440968B2

Reaction notes

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