Formic Acid → HCID 178481857, compound

HRID 2283189Notes

Reaction equation

HRID 2283189 reaction equation
[F:1][CH:2]([F:11])[C:3](=O)[CH2:4][C:5](OCC)=[O:6].C(O)=O.[CH3:15][NH:16][NH2:17]>C(OC)(C)(C)C>[F:1][CH:2]([F:11])[C:3]1[CH:4]=[C:5]([OH:6])[N:16]([CH3:15])[N:17]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 6061MethylhydrazineHCID 67697Ethyl 4,4-difluoroacetoacetate

Product 1

HCID 178481857HCID 178481857, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
5 °C

Procedure

166 g (1 mol) of ethyl 4,4-difluoro-3-oxobutanoate were charged in 500 ml of methyl tert-butyl ether and treated with 140 g of formic acid. After cooling of the mixture to 5° C., 119 g (as 40% aqueous solution) of monomethylhydrazine were added. The mixture was then stirred for 20 h at 22° C. The phases were separated, and the organic phase was washed with 200 ml of water and dried over MgSO4. After the removal of the solvent under reduced pressure, 148 g of the product was obtained as an yellow solid having an m.p. of 133° C. and a purity of 95%. Yield 95%.

Workup

  1. customThe phases were separated
  2. washthe organic phase was washed with 200 ml of water
  3. dry with materialdried over MgSO4
  4. customAfter the removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-7625eac0e79144fa8234a02130d7736d
Source dataset
uspto-grants-2015_09
Patent number
US09145369B2

Reaction notes

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