Hydrazine hydrate (1:1) → HCID 59242657, compound

HRID 1630456Notes

Reaction equation

HRID 1630456 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3](=O)[C:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[CH:5][C:6](O)=[O:7].O.[NH2:19][NH2:20]>C(#N)C.C(O)(=O)C.ClCCl>[C:9]1([C:4]2[C:3]([C:2]([F:17])([F:16])[F:1])=[N:20][NH:19][C:6](=[O:7])[CH:5]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 68458790HCID 68458790, compound

Product 1

HCID 59242657HCID 59242657, compoundYield 102.6%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5,5,5-trifluoro-4-oxo-3-phenyl-pent-2-enoic acid (D1) (22.6 g, 0.084 mol) in a mixture of acetonitrile (150 ml) and acetic acid (15 ml), was added hydrazine hydrate (7.75 ml, 0.148 mol). The reaction mixture was heated at reflux for 16 h, cooled to room temperature, diluted with dichloromethane and then extracted with 0.5 M hydrochloric acid (150 ml). The organic layer was separated, dried (Na2SO4) and the solvent evaporated in vacuo to yield D2 (20.7 g, 100%) as a mixture of isomers (75/5 ratio by LCMS). C11H7F3N2O requires 240; Found 239 (M-H)−.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 16 h
  3. extractionextracted with 0.5 M hydrochloric acid (150 ml)
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-7d519de6b3f94ff2876476365f787edf
Source dataset
uspto-grants-2014_07
Patent number
US08791120B2

Reaction notes

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