Methyl trifluoromethyl ketone → HCID 178465586, compound

HRID 1823335Notes

Reaction equation

HRID 1823335 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([CH3:5])=O.[Cl:8][C:9]1[C:10]([NH:15][NH2:16])=[N:11][CH:12]=[CH:13][CH:14]=1>>[F:1][C:2]([F:7])([F:6])[C:3](=[N:16][N:15]=[C:10]1[C:9]([Cl:8])=[CH:14][CH:13]=[CH:12][NH:11]1)[CH3:5]

Participants

3

Reactant 2

HCID 9871Methyl trifluoromethyl ketoneHCID 5561003-Chloro-2-hydrazinylpyridine2×

Product 1

HCID 178465586HCID 178465586, compoundYield 66%

Procedure

1,1,1-Trifluoroacetone (7.80 g, 69.6 mmol) was added to (3-chloro-pyridin-2-yl)-hydrazine (alternatively named (3-chloro-pyridin-2-yl)-hydrazine) (10 g, 69.7 mmol) at 20–25° C. After the addition was complete, the mixture was stirred for about 10 minutes. The solvent was removed under reduced pressure, and the mixture was partitioned between ethyl acetate (100 mL) and saturated sodium carbonate solution (100 mL). The organic layer was dried and evaporated. Chromatography on silica gel (eluted with ethyl acetate) gave the product as an off-white solid (11 g, 66% yield), m.p. 64–64.5° C. (after crystallization from ethyl acetate/hexanes).

Workup

  1. additionAfter the addition
  2. customThe solvent was removed under reduced pressure
  3. customthe mixture was partitioned between ethyl acetate (100 mL) and saturated sodium carbonate solution (100 mL)
  4. customThe organic layer was dried
  5. customevaporated
  6. customChromatography on silica gel (eluted with ethyl acetate) gave

Sources & evidence

ORD record
ord-3db5688578664d489cd67d3c591168b4
Source dataset
uspto-grants-2006_05
Patent number
US07038057B2

Reaction notes

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