Formic Acid → 5-Formamido-1-methylpyrazole

HRID 373425Notes

Reaction equation

HRID 373425 reaction equation
C(O[C:5](=[O:7])C)(=O)C.C(O)=O.[NH2:11][C:12]1[N:16]([CH3:17])[N:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.O>[CH:5]([NH:11][C:12]1[N:16]([CH3:17])[N:15]=[CH:14][CH:13]=1)=[O:7]

Participants

7

Reactant 4

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 1369272-Methyl-2H-pyrazol-3-ylamine

Product 1

HCID 27558695-Formamido-1-methylpyrazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of acetic anhydride (38.86 ml) and formic acid (15.54 ml) was stirred at 45° C. for 45 minutes. To this mixture was added 5-amino-1-methylpyrazole (10 g) under ice-cooling, and the reaction mixture was stirred at the same temperature for 10 minutes. The resultant mixture was poured into a mixture of water and ethyl acetate, and the resultant solution was adjusted to pH 8 with potassium carbonate. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate six times. The organic layers were combined, dried over magnesium sulfate, and evaporated in vacuo to give 5-formamido-1-methylpyrazole (12.88 g).

Workup

  1. temperaturecooling
  2. stirringthe reaction mixture was stirred at the same temperature for 10 minutes
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate six times
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-2bc05f1a68714676bc5a846a0326063a
Source dataset
uspto-grants-1992_11
Patent number
US05162520

Reaction notes

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