Methanol → 1-isobutyl-1H-pyrazol-3-amine

HRID 546063Notes

Reaction equation

HRID 546063 reaction equation
[N+:1]([C:4]1[CH:8]=[CH:7][N:6]([CH2:9][CH:10]([CH3:12])[CH3:11])[N:5]=1)([O-])=O.CO.[H][H]>C(OCC)(=O)C.[Pd]>[CH2:9]([N:6]1[CH:7]=[CH:8][C:4]([NH2:1])=[N:5]1)[CH:10]([CH3:12])[CH3:11]

Participants

6

Reactant 3

HCID 887MethanolHCID 25247760HCID 25247760, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 196198391-isobutyl-1H-pyrazol-3-amineYield 86.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

3-Nitro-1-iso-butyl-1H-pyrazole (83 mg, 0.49 mmol) was dissolved in ethyl acetate (3 mL) and methanol (3 mL) was added. Palladium, 10 wt. % on activated carbon, wet (˜50 mg) was added to the reaction. The vial was charged with hydrogen gas (via balloon) and the reaction stirred for 16 h at 25° C. The reaction was passed through a plug of celite and concentrated in vacuo to afford 1-iso-butyl-1H-pyrazol-3-ylamine (59 mg, 86%) as a golden oil: ESI-LRMS m/e calcd for C7H13N3 [M+] 139.1, found 140.3 [M+H+].

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-43fbb088e0164f5cac06e1ae909979e2
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

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