Ethanol → HCID 178481740, compound

HRID 1604945Notes

Reaction equation

HRID 1604945 reaction equation
[C:1]([C:3]1[C:4]([C:14]2O[C:16]([N+:19]([O-:21])=[O:20])=[CH:17][CH:18]=2)=[N:5][N:6]([CH3:13])[C:7]=1[N:8]=[CH:9]OCC)#[N:2].Cl.[NH2:23][OH:24].C(O)C.[OH-:28].[Na+]>O>[NH2:2][C:1]1[N+:23]([O-:24])=[CH:9][N:8]=[C:7]2[N:6]([CH3:13])[N:5]=[C:4]([C:14]3[O:28][C:16]([N+:19]([O-:21])=[O:20])=[CH:17][CH:18]=3)[C:3]=12

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 54229099HCID 54229099, compound

Product 1

HCID 178481740HCID 178481740, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 14.4 grams of 4-cyano-5-ethoxymethylene amino-1-methyl-3-(5-nitro-2-furyl)-pyrazole, 3.5 grams of hydroxylamine hydrochloride, 150 milliliters of ethanol and a solution containing 2.0 grams of sodium hydroxide dissolved in 10 milliliters of water was heated at reflux for 1 hour and cooled. The crystalline product was filtered, washed with ethanol and dried. Recrystallisation from water gave 4-amino-1-methyl-3-(5-nitro-2-furyl)-1H-pyrazolo[3,4-d]pyrimidin-5-oxide having melting point 285°C; melting point, infra-red and proton NMR spectra being identical with the product obtained in Example 20.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. temperaturecooled
  4. filtrationThe crystalline product was filtered
  5. washwashed with ethanol
  6. customdried
  7. customRecrystallisation from water

Sources & evidence

ORD record
ord-10c33d421d2c407083a47d1edb6f885a
Source dataset
uspto-grants-1976_04
Patent number
US03948913

Reaction notes

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