Phosphorus oxychloride → Dimethyl 4-chloropyridine-3,5-dicarboxylate
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
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
- temperatureThe mixture was cooled to RT
- additionpoured into ice
- extractionextracted with ether
- washThe organic layer was washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-d14a058bf7e8446199a5ef4d0ec86e68
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09440968B2
Reaction notes
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