Methyl trifluoromethyl ketone → HCID 178465586, compound

HRID 1268898Notes

Reaction equation

HRID 1268898 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-hydrazinylpyridine

Product 1

HCID 178465586HCID 178465586, compoundYield 66.5%

Procedure

1,1,1-Trifluoroacetone (7.80 g, 69.6 mmol) was added to (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-67f6284733ac41d6a24f3790f4dfbcf9
Source dataset
uspto-grants-2007_04
Patent number
US07199138B2

Reaction notes

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