Phosphorus oxychloride → HCID 117992232, compound

HRID 530981Notes

Reaction equation

HRID 530981 reaction equation
P(Cl)(Cl)([Cl:3])=O.O[C:7]1[C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]([C:17]([O:19][CH3:20])=[O:18])=[C:9]([CH3:21])[N:8]=1.C(=O)(O)[O-].[Na+]>C(#N)C>[Cl:3][C:7]1[C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]([C:17]([O:19][CH3:20])=[O:18])=[C:9]([CH3:21])[N:8]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178498314HCID 178498314, compound

Product 1

HCID 117992232HCID 117992232, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Phosphorus oxychloride (4.11 mL) was added to a mixture of dimethyl 2-hydroxy-6-methylpyridine-3,5-dicarboxylate (4.96 g) and acetonitrile (30 mL), and the resultant mixture was stirred overnight at 90° C. in a nitrogen atmosphere. The reaction mixture was allowed to cool to room temperature, and then, a saturated aqueous solution of sodium bicarbonate was added thereto, followed by extraction with ethyl acetate. The obtained organic layer was dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (4.97 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe obtained organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-174bdaea177248bfb6a496cd69ef4e64
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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