Phenylphosphonic dichloride → 2-Chloro-3,4-diethoxycarbonyl-6-methyl-5-nitropyridine

HRID 37476

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:7](=O)[NH:8][C:9]([CH3:20])=[C:10]([N+:17]([O-:19])=[O:18])[C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:5])[CH3:2].C1(P(Cl)([Cl:30])=O)C=CC=CC=1>O>[Cl:30][C:7]1[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:10]([N+:17]([O-:19])=[O:18])=[C:9]([CH3:20])[N:8]=1

Participants

Conditions

Temperature: 170 °C

Procedure

To 1.0 g of 3,4-diethoxycarbonyl-6-methyl-5-nitro-2-pyridone was added 1.3 ml (3.2 eq.) of phenylphosphonic dichloride. The mixture was heated at 170° C. for 20 mintues. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. After the solvent was distilled off, the residue was purified by silica gel column chromatography (eluent:ethyl acetate) to give an oily product.

Workup

extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed with water
dry with materiala saturated aqueous solution of sodium chloride and dried over magnesium sulfate
distillationAfter the solvent was distilled off
customthe residue was purified by silica gel column chromatography (eluent:ethyl acetate)
customto give an oily product

Sources & evidence

ORD record: ord-1ee93671a1c449ee91ceaa24da712e78
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05420275

Linked notes

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