Acetic Acid → HCID 19432752, compound

HRID 1736561Notes

Reaction equation

HRID 1736561 reaction equation
[OH-].[Na+].OO.[OH:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH:7]1[N:11]1[C:15]([NH2:16])=[C:14]([C:17]#[N:18])[C:13]([CH3:19])=[N:12]1.C(O)(=[O:22])C>O>[OH:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH:7]1[N:11]1[C:15]([NH2:16])=[C:14]([C:17]([NH2:18])=[O:22])[C:13]([CH3:19])=[N:12]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen Peroxide2×HCID 14798Sodium HydroxideHCID 19432769HCID 19432769, compound

Product 1

HCID 19432752HCID 19432752, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of sodium hydroxide (1.2 g, 30 mmol) in water (50 ml) in an ice-bath was added 30% hydrogen peroxide (3.3 ml, 29 mmol). The reaction mixture was stirred for 5 minutes then 1-(2-hydroxycyclopentyl)-3-methyl-5-amino-1H-pyrazole-4-carbonitrile (2.5 g, 12 mmol) was added. The reaction mixture was stirred in an ice-bath for 5 hours, additional 30% hydrogen peroxide (1.5 ml) was added and stirring was continued for 2 hours. Acetic acid (2 ml) was added to the reaction mixture, all but approximately 25 ml of the solvent was removed in vacuo and the resulting solid was collected by filtration and washed with water. The solid was air dried to afford 2.4 g (90%) of 1-(2-hydroxycyclopentyl)-3-methyl-5-amino-1H-pyrazole-4-carboxamide as a white solid, m.p. 120°-124° C. (dec.).

Workup

  1. stirringThe reaction mixture was stirred in an ice-bath for 5 hours
  2. stirringstirring
  3. waitwas continued for 2 hours
  4. customall but approximately 25 ml of the solvent was removed in vacuo
  5. filtrationthe resulting solid was collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-068ee59fcda245efac0ae6998cf30cbf
Source dataset
uspto-grants-1996_07
Patent number
US05541187

Reaction notes

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