Phosphorus oxychloride → HCID 117992748, compound

HRID 531113Notes

Reaction equation

HRID 531113 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH2:6]([C:8]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][C:11]([C:18]([O:20][CH3:21])=[O:19])=[C:10](O)[N:9]=1)[CH3:7].C(=O)([O-])O.[Na+]>C(#N)C>[Cl:3][C:10]1[C:11]([C:18]([O:20][CH3:21])=[O:19])=[CH:12][C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:8]([CH2:6][CH3:7])[N:9]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178437791HCID 178437791, compound

Product 1

HCID 117992748HCID 117992748, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

Phosphoryl trichloride (17.3 ml) was added to a solution of dimethyl 2-ethyl-6-hydroxypyridine-3,5-dicarboxylate (22.3 g) in acetonitrile (250 mL) at room temperature. The mixture was stirred at 90° C. under nitrogen atmosphere for 3 hours. The mixture was neutralized with aqueous saturated sodium hydrogen carbonate solution at 0° C. and extracted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to give the title compound (24.0 g).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2565ebe46bc04cef97f214b9bf705299
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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