Hydrazine hydrate (1:1) → HCID 59242648, compound

HRID 1485855Notes

Reaction equation

HRID 1485855 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3](=O)[C:4]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)=[CH:5][C:6](O)=[O:7].O.[NH2:20][NH2:21]>C(O)C.C(O)(=O)C.ClCCl>[F:15][C:12]1[CH:13]=[CH:14][C:9]([C:4]2[C:3]([C:2]([F:18])([F:17])[F:1])=[N:21][NH:20][C:6](=[O:7])[CH:5]=2)=[CH:10][CH:11]=1

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 68458802HCID 68458802, compound

Product 1

HCID 59242648HCID 59242648, compoundYield 70.2%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5,5,5-trifluoro-3-(4-fluorophenyl)-4-oxo-pent-2-enoic acid (D5) (1.4 g, 5.3 mmol) in a mixture of ethanol (10 ml) and acetic acid (1 ml), was added hydrazine hydrate (0.49 ml, 9.33 mmol). 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 D6 (0.96 g, 70%) as a mixture of isomers. C11H6F4N2O requires 258; Found 259 (MH+).

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-0ccb5aaa26ff465582ebfbeb84437dfc
Source dataset
uspto-grants-2016_08
Patent number
US09422296B2

Reaction notes

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