Sodium Acetate → 2-(Acetoxymethyl)-6-chloroisonicotinic acid

HRID 623631Notes

Reaction equation

HRID 623631 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([Cl:13])[N:12]=1)[C:6]([O:8]C)=[O:7].[C:14]([O-:17])(=[O:16])[CH3:15].[Na+]>CN(C)C(=O)C.O>[C:14]([O:17][CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([Cl:13])[N:12]=1)[C:6]([OH:8])=[O:7])(=[O:16])[CH3:15]

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 86225002Methyl 2-(bromomethyl)-6-chloropyridine-4-carboxylate

Product 1

HCID 874269902-(Acetoxymethyl)-6-chloroisonicotinic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of methyl 2-(bromomethyl)-6-chloroisonicotinate and sodium acetate in N,N-dimethylacetamide is stirred at 120° C. for 2 hours. The mixture is cooled to room temperature and diluted with water (50 mL). The mixture is washed with ethyl acetate/toluene (2:1, 80 mL×2). Water layer is acidified (to pH 4) by the addition of 2M hydrochloric acid, extracted with ethyl acetate (80 mL×2), dried over sodium sulfate. The organic solvent is removed under reduced pressure to give the title compound as a crude product (590 mg, clear brown oil, include N,N-dimethylacetamide). This is used without purification in the next step.

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. washThe mixture is washed with ethyl acetate/toluene (2:1, 80 mL×2)
  3. additionby the addition of 2M hydrochloric acid
  4. extractionextracted with ethyl acetate (80 mL×2)
  5. dry with materialdried over sodium sulfate
  6. customThe organic solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-b812e295a2e94b0e99db15c15cb13005
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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