Diisopropyl Ether → 5-Amino-1-methyl-4-nitrosopyrazole

HRID 1247770Notes

Reaction equation

HRID 1247770 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][CH:3]=1.[N:8](OCCC(C)C)=[O:9].C(OC(C)C)(C)C>C(O)C.Cl>[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[N:8]=[O:9]

Participants

6

Reactant 3

HCID 7914Diisopropyl EtherHCID 8053Isoamyl NitriteHCID 1369272-Methyl-2H-pyrazol-3-ylamine

Product 1

HCID 128515805-Amino-1-methyl-4-nitrosopyrazole

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

To a solution of 5-amino-1-methylpyrazole (5 g) in ethanol (50 ml) was added isoamyl nitrite (6.92 ml), and then 20% hydrochloric acid (5 drops) was added at 4° C. The reaction mixture was refluxed for 2 hours and cooled to room temperature. To the reaction mixture was added diisopropyl ether (50 ml), and the mixture was stirred for 0.5 hour. The resulting precipitate was collected by filtration and dried in vacuo to give 5-amino-1-methyl-4-nitrosopyrazole (3.53 g).

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hours
  2. filtrationThe resulting precipitate was collected by filtration
  3. customdried in vacuo

Sources & evidence

ORD record
ord-a7ce45b10f9b4f009f5e405abac47037
Source dataset
uspto-grants-2006_10
Patent number
US07129232B2

Reaction notes

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