Citric Acid → HCID 23284668, compound

HRID 369245Notes

Reaction equation

HRID 369245 reaction equation
C[O-].[Na+].[F:4][C:5]1[C:14]([CH3:15])=[C:13]([N+:16]([O-:18])=[O:17])[C:12](F)=[CH:11][C:6]=1[C:7]([O:9]C)=[O:8].C(O)(=O)C[C:22](CC(O)=O)(C(O)=O)[OH:23]>C(#N)C>[F:4][C:5]1[C:14]([CH3:15])=[C:13]([N+:16]([O-:18])=[O:17])[C:12]([O:23][CH3:22])=[CH:11][C:6]=1[C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 10942334Sodium MethoxideHCID 23284769HCID 23284769, compound

Product 1

HCID 23284668HCID 23284668, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

Sodium methoxide (28% methanol solution; 1.66 g) was added to a solution of methyl 2,5-difluoro-3-methyl-4-nitrobenzoate (1.0 g) in acetonitrile (5 ml) under ice cooling, and the mixture was stirred for 1 hour at 0° C. and for 2 hours at 50° C. The reaction mixture was additionally stirred overnight at room temperature and then poured into ice water. The mixture was acidified with citric acid and then extracted with diethyl ether. An organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Diethyl ether was added to the residue, and insoluble matter was removed by filtration. The filtrate was concentrated under reduced pressure to obtain the title compound (1.1 g).

Workup

  1. waitThe reaction mixture was additionally stirred overnight at room temperature
  2. extractionextracted with diethyl ether
  3. dry with materialAn organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionDiethyl ether was added to the residue, and insoluble matter
  6. customwas removed by filtration
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b6994c5ac33c4f74adc6251af3c7cb1d
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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