Acetic Acid → 3-Amino-6-fluoro-4,5-diethoxycarbonyl-2-phenylpyridine

HRID 37493Notes

Reaction equation

HRID 37493 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([F:26])=[N:8][C:9]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:10]([N+:17]([O-])=O)[C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:5])[CH3:2].C(O)(=O)C>C(O)C>[NH2:17][C:10]1[C:9]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[N:8][C:7]([F:26])=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 199356173,4-Diethoxycarbonyl-2-fluoro-5-nitro-6-phenylpyridine

Product 1

HCID 152896983-Amino-6-fluoro-4,5-diethoxycarbonyl-2-phenylpyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 5 ml of ethanol was dissolved 160 mg of 3,4-diethoxycarbonyl-2-fluoro-5-nitro-6-phenylpyridine, and 120 mg (5 eq.) of reduced iron was added to the solution, followed by addition of 0.5 ml (20 eq.) of acetic acid. After the mixture was refluxed for 30 minutes, the solvent was distilled off. The residue was neutralized with sodium hydrogencarbonate, followed by extraction with ethyl acetate. After the precipitate was removed by filtration, the obtained organic layer was washed with water and a saturated aqueous solution of sodium chloride, and dried. Then, the solvent was distilled off.

Workup

  1. additionwas added to the solution
  2. temperatureAfter the mixture was refluxed for 30 minutes
  3. distillationthe solvent was distilled off
  4. extractionfollowed by extraction with ethyl acetate
  5. customAfter the precipitate was removed by filtration
  6. washthe obtained organic layer was washed with water
  7. dry with materiala saturated aqueous solution of sodium chloride, and dried
  8. distillationThen, the solvent was distilled off

Sources & evidence

ORD record
ord-fc02068cd0c1425ea5a7e41355468849
Source dataset
uspto-grants-1995_05
Patent number
US05420275

Reaction notes

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