Ethyl Acetate → HCID 178434304, compound

HRID 1992309Notes

Reaction equation

HRID 1992309 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1F)=O.[NH2:14][NH2:15].CCOC(C)=O>C(O)CO>[CH3:1][C:2]1[C:4]2[C:5](=[CH:6][CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=2)[NH:15][N:14]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 9321HydrazineHCID 27810671-(2-Fluoro-5-nitrophenyl)ethan-1-one

Product 1

HCID 178434304HCID 178434304, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A solution of 2-fluoro-5-nitroacetophenone (1.57 g, 8.6 mmol) in ethylene glycol (50 mL) was added hydrazine (0.29 g, 9.0 mmol) was stirred for 2 h at room temperature and then heated at 165° C. for 24 h. The reaction mixture was cooled to room temperature, poured over EtOAc (100 mL), and extracted with H2O (2×100 mL). The organic layers was dried over Na2SO4 and the solvent was removed in vacuo. The crude product was purified by silica gel chromatography to afford a light yellow solid (0.8 g, 53%) Rf=0.2 (EtOAc/hexane, 1/3). 1H NMR CDCl3 δ 8.63 (s, 1H), 8.23 (d, 2H, J=3 Hz), 7.46 (d, 1H, J=3 Hz), 2.60 (s, 3H).

Workup

  1. temperatureheated at 165° C. for 24 h
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionextracted with H2O (2×100 mL)
  4. dry with materialThe organic layers was dried over Na2SO4
  5. customthe solvent was removed in vacuo
  6. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-300af4f026694063a7c287246751cdd2
Source dataset
uspto-grants-2010_01
Patent number
US07648986B2

Reaction notes

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