Formic Acid → 5-Formamido-1-(2-hydroxyethyl)pyrazole

HRID 1710285Notes

Reaction equation

HRID 1710285 reaction equation
[C:1](OC(=O)C)(=[O:3])C.C(O)=O.[NH2:11][C:12]1[N:16]([CH2:17][CH2:18][OH:19])[N:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>O>[CH:1]([NH:11][C:12]1[N:16]([CH2:17][CH2:18][OH:19])[N:15]=[CH:14][CH:13]=1)=[O:3]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 3202812-(5-amino-1H-pyrazol-1-yl)ethan-1-ol

Product 1

HCID 150777375-Formamido-1-(2-hydroxyethyl)pyrazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of acetic anhydride (44.5 ml) and formic acid (22.3 ml) was stirred at room temperature for an hour. To this mixture was added 5-amino-1-(2-hydroxyethyl)pyrazole (30 g) at 0°-10° C., and the mixture was stirred under ice-cooling for 30 minutes. The mixture was poured into ice-cooled water, adjusted to pH 10.5 with 40% potassium carbonate solution, and stirred under ice-cooling for 30 minutes. The mixture was extracted with a mixture of tetrahydrofuran and ethyl acetate 6 times. The organic layer was dried over magnesium sulfate, and evaporated in vacuo to give 5-formamido-1-(2-hydroxyethyl)pyrazole (30.8 g).

Workup

  1. stirringthe mixture was stirred under ice-
  2. temperaturecooling for 30 minutes
  3. additionThe mixture was poured into ice-
  4. stirringstirred under ice-
  5. temperaturecooling for 30 minutes
  6. extractionThe mixture was extracted with a mixture of tetrahydrofuran and ethyl acetate 6 times
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-9bab88a66c4c4f2189a6bf116606f0d7
Source dataset
uspto-grants-1990_08
Patent number
US04952578

Reaction notes

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