Ethyl Acetate → HCID 67400720, compound

HRID 1186449Notes

Reaction equation

HRID 1186449 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([O:9][CH:10]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[C:11]([F:14])([F:13])[F:12])[C:6]([N+:21]([O-])=O)=[CH:5][CH:4]=1.C(OCC)(=O)C>C(O)(=O)C.O.[Cl-].[Na+].O>[CH3:1][O:2][C:3]1[N:8]=[C:7]([O:9][CH:10]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[C:11]([F:12])([F:13])[F:14])[C:6]([NH2:21])=[CH:5][CH:4]=1

Participants

6

Reactant 2

HCID 8857Ethyl AcetateHCID 67402350HCID 67402350, compound

Product 1

HCID 67400720HCID 67400720, compoundYield 41%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

6-Methoxy-3-nitro-2-[2,2,2-trifluoro-1-(pyridin-3-yl)-ethoxy]pyridine (243 mg, 0.738 mmol) was dissolved in acetic acid (3.6 mL) and water (3.6 mL). To this, reduced iron (124 mg, 2.21 mmol) was added under a nitrogen atmosphere at room temperature and the mixture was stirred for 1.7 hours. After water and brine were added to the reaction mixture, extraction with ethyl acetate was performed, followed by washing with saturated sodium bicarbonate and brine, and drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by preparative thin-layer chromatography (chloroform/methanol=30/1) to give Compound HA (89.6 mg, yield: 41%).

Workup

  1. washby washing with saturated sodium bicarbonate and brine
  2. dry with materialdrying over anhydrous sodium sulfate
  3. customThe solvent was evaporated off under reduced pressure
  4. customthe residue was purified by preparative thin-layer chromatography (chloroform/methanol=30/1)
  5. customto give Compound HA (89.6 mg, yield: 41%)

Sources & evidence

ORD record
ord-79981f83432641369e9fa2d02a8a5132
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

Loading…