Hydrochloric Acid → 6-Methyl-3-(3-nitro-phenyl)pyrazolo[5,1-c][1,2,4]triazole

HRID 1742066Notes

Reaction equation

HRID 1742066 reaction equation
C([N:4]1[C:8]2=[CH:9][C:10]([CH3:12])=[N:11][N:7]2[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=2)=[N:5]1)(=O)C.[OH-].[Na+].Cl>CO>[CH3:12][C:10]1[CH:9]=[C:8]2[N:4]=[N:5][CH:6]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=3)[N:7]2[N:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 190101071-Acetyl-6-methyl-3-(3-nitro-phenyl)pyrazolo[5,1-c][1,2,4]triazole

Product 1

HCID 678499026-Methyl-3-(3-nitro-phenyl)pyrazolo[5,1-c][1,2,4]triazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

500 mg (1.75 mmol) of 1-acetyl-6-methyl-3-(3-nitro-phenyl)pyrazolo[5,1-c][1,2,4]triazole are mixed with 7 ml of methanol and 3 ml of 2N sodium hydroxide solution and heated at boiling point until a clear solution is produced, then cooled down and acidified with 2N hydrochloric acid. The precipitate formed is filtered off under suction, washed neutral with water and then washed with a little methanol and a little ethyl acetate. After recrystallisation from DMSO, 400 mg (94%) of 6-methyl-3-(3-nitro-phenyl)pyrazolo[5,1-c][1,2,4]triazole with a m. pt. of 269°-275° C. (decomposes from 247° C.) are obtained.

Workup

  1. temperatureheated
  2. customis produced
  3. temperaturecooled down
  4. customThe precipitate formed
  5. filtrationis filtered off under suction
  6. washwashed neutral with water
  7. washwashed with a little methanol
  8. customAfter recrystallisation from DMSO, 400 mg (94%) of 6-methyl-3-(3-nitro-phenyl)pyrazolo[5,1-c][1,2,4]triazole with a m. pt. of 269°-275° C. (decomposes from 247° C.)
  9. customare obtained

Sources & evidence

ORD record
ord-75e4f98f9f4f4694ac71ea3a1a4d9bac
Source dataset
uspto-grants-1994_08
Patent number
US05336780

Reaction notes

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