Ethanol → HCID 178434471, compound

HRID 1157409Notes

Reaction equation

HRID 1157409 reaction equation
F[C:2]1[C:7]([C:8](=O)[CH3:9])=[CH:6][CH:5]=[C:4]([F:11])[N:3]=1.O.[NH2:13][NH2:14].O.CCO>C(Cl)Cl.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[F:11][C:4]1[N:3]=[C:2]2[NH:13][N:14]=[C:8]([CH3:9])[C:7]2=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 251322441-(2,6-Difluoropyridin-3-yl)ethanone

Product 1

HCID 178434471HCID 178434471, compound

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 7.46 g (47.51 mmol) of 1-(2,6-difluoropyridin-3-yl)ethanone (37-2) in 50 mL of CH2Cl2 under nitrogen was added dropwise titanium (IV) isopropoxide. The resulting solution was stirred vigorously for 15 minutes before hydrazine hydrate (4.62 g, 95.0 mmol) was added slowly to form a thick slurry. The reaction mixture was stirred for 1 hour before the addition of 11 mL of H2O, and the resulting mixture stirred for 1.5 hours until completion as determined by LC/MS analysis. The solid matter was filtered off and the filterate was condensed to yield a white solid. EtOH (100 mL) was added to the crude intermediate and the mixture was heated to reflux for 6 hours. After the reaction was complete as determined by LC/MS analysis the solvent was removed to yield the desired product. No further purification was necessary. 1H NMR (CDCl3): 2.56 (s, 3H), 6.78 (d, 1H), 8.08 (t, 1H).

Workup

  1. additionwas added slowly
  2. customto form a thick slurry
  3. filtrationThe solid matter was filtered off
  4. customcondensed
  5. customto yield a white solid
  6. temperaturethe mixture was heated
  7. temperatureto reflux for 6 hours
  8. customwas removed

Sources & evidence

ORD record
ord-1b8b409aeb5b4d4cb1e1372695165ba1
Source dataset
uspto-grants-2010_10
Patent number
US07807684B2

Reaction notes

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