Hydrazine hydrate (1:1) → HCID 178506286, compound

HRID 711094Notes

Reaction equation

HRID 711094 reaction equation
O.[NH2:2][NH2:3].[Br:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=O)[C:12]([F:15])([F:14])[F:13])=[C:7](F)[CH:6]=1>C(O)CCC.O>[Br:4][C:5]1[CH:6]=[C:7]2[C:8]([C:11]([C:12]([F:15])([F:14])[F:13])=[N:2][NH:3]2)=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 669578641-(4-Bromo-2-fluorophenyl)-2,2,2-trifluoroethan-1-one

Product 1

HCID 178506286HCID 178506286, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 962WaterSolvent

Procedure

Hydrazine hydrate (3.5 mL, 45 mmol) was added to a solution of 1-(4-bromo-2-fluorophenyl)-2,2,2-trifluoroethanone (1.00 g, 3.69 mmol) in 1-butanol (15 mL). The reaction was heated to reflux for 5 hours, then cooled to room temperature and left stirring overnight. The reaction was diluted with water (50 mL) and extracted with ethyl acetate (3×). The combined organics were washed with brine, dried over magnesium sulfate, filtered, and concentrated. Purification by flash column chromatography (0-50% ethyl acetate/heptanes) gave the title compound (310 mg, 32%) as an off-white solid. 1H NMR (400 MHz, CDCl3, δ): 7.42 (dd, J=8.58, 1.56 Hz, 1H), 7.72 (d, J=8.58 Hz, 1H), 7.75 (dd, J=1.56, 0.78 Hz, 1H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 5 hours
  3. waitleft
  4. extractionextracted with ethyl acetate (3×)
  5. washThe combined organics were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by flash column chromatography (0-50% ethyl acetate/heptanes)

Sources & evidence

ORD record
ord-38f621833a4442918c3caed7393fcaf2
Source dataset
uspto-grants-2015_11
Patent number
US09181252B2

Reaction notes

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