Sodium Bicarbonate → 3,4-Diethoxycarbonyl-2-fluoro-5-nitro-6-phenylpyridine

HRID 37492Notes

Reaction equation

HRID 37492 reaction equation
N[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:5]([N+:18]([O-:20])=[O:19])=[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:3]=1.B(F)(F)[F:28].F.N([O-])=O.[Na+].C(=O)([O-])O.[Na+]>C(O)(=O)C.O>[CH2:11]([O:10][C:8]([C:7]1[C:2]([F:28])=[N:3][C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:5]([N+:18]([O-:20])=[O:19])[C:6]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:9])[CH3:12]

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 9855450Trifluoroborane HydrofluorideHCID 199356032-Amino-3,4-diethoxycarbonyl-5-nitro-6-phenylpyridineHCID 23668193Sodium Nitrite

Product 1

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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
-5 °C

Procedure

In 2 ml of acetic acid was dissolved 100 mg of 2-amino-3,4-diethoxycarbonyl-5-nitro-6-phenylpyridine, and 1.5 ml of 42% hydrofluoroboric acid was added to the solution. The mixture was cooled to -5° C., followed by adding dropwise a solution of 21 mg (1.1 eq) of sodium nitrite dissolved in 0.5 ml of water. Thirty minutes later, the temperature of the mixture was elevated to room temperature and the mixture was neutralized with sodium hydrogencarbonate, followed by extraction with ethyl acetate. After the organic layer was washed with water and a saturated aqueous solution of sodium chloride, and dried. After the solvent was distilled off, the resulting crystals (2-pyridone compound) were collected by filtration with hexane, and washed. The solvent was distilled off from the obtained filtrate, to give an oily substance.

Workup

  1. additionwas added to the solution
  2. customThirty minutes
  3. customwas elevated to room temperature
  4. extractionfollowed by extraction with ethyl acetate
  5. washAfter the organic layer was washed with water
  6. dry with materiala saturated aqueous solution of sodium chloride, and dried
  7. distillationAfter the solvent was distilled off
  8. filtrationthe resulting crystals (2-pyridone compound) were collected by filtration with hexane
  9. washwashed
  10. distillationThe solvent was distilled off from the obtained filtrate
  11. customto give an oily substance

Sources & evidence

ORD record
ord-4afe1d8998b646889314d45135528e41
Source dataset
uspto-grants-1995_05
Patent number
US05420275

Reaction notes

Loading…