Hydrazine hydrate (1:1) → HCID 86745082, compound

HRID 728799Notes

Reaction equation

HRID 728799 reaction equation
[CH3:1][C:2]([CH3:22])([CH3:21])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][N:9]=[CH:8][C:7]=1[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[F:20])=O)=[O:4].O.[NH2:24][NH2:25]>C(O)C>[CH3:1][C:2]([CH3:22])([CH3:21])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][N:9]=[CH:8][C:7]=1[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[F:20])=[N:24][NH2:25])=[O:4]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 15008328HCID 15008328, compound

Product 1

HCID 86745082HCID 86745082, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of [4-(2,2-dimethylpropionamido)-3-pyridinyl]-2-fluorophenylmethanone (9.8 g)and hydrazine monohydrate (3.3 g) in 100 mL ethanol was stirred at reflux for five hours, cooled, stirred with ice-water and extracted with ethyl acetate-ether. The dried organic layer was filtered and evaporated. The residue was eluted through silica with dichloromethane then 15% ethyl acetate in dichloromethane via flash column chromatography and then was triturated with hexane-ether to yield 7 g of [4-(2,2-dimethylpropionamido)-3-pyridinyl]-2-fluorophenylmethanone-hydrazone, as a solid, m.p. 78°-82° C. Four grams were converted to the maleate salt in methanol-ether and thereafter recrystallized from methanol-ether to yield 2.3 g of crystals, d 161°-162° C.

Workup

  1. temperatureat reflux for five hours
  2. temperaturecooled
  3. extractionextracted with ethyl acetate-ether
  4. filtrationThe dried organic layer was filtered
  5. customevaporated
  6. washThe residue was eluted through silica with dichloromethane
  7. custom15% ethyl acetate in dichloromethane via flash column chromatography and then was triturated with hexane-ether

Sources & evidence

ORD record
ord-4972fd1de1464cc587018a8666a50636
Source dataset
uspto-grants-1991_09
Patent number
US05051430

Reaction notes

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