Methanol → 1-Propyl-1 H-pyrazol-3-ylamine

HRID 546043Notes

Reaction equation

HRID 546043 reaction equation
[N+:1]([C:4]1[CH:8]=[CH:7][N:6]([CH2:9][CH2:10][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)[CH2:10][CH3:11]

Participants

6

Reactant 3

HCID 887MethanolHCID 19616496HCID 19616496, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70177711-Propyl-1 H-pyrazol-3-ylamineYield 73.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

3-Nitro-1-propyl-1H-pyrazole (92 mg, 0.59 mmol) was dissolved in ethyl acetate (3 mL) and methanol (3 mL) was added. Palladium, 10 wt. % on carbon, wet (˜50 mg) was added to the mixture. The vial was charged with hydrogen gas (via balloon) and the mixture was stirred for 16 h at 25° C. The mixture was passed through a plug of celite and concentrated in vacuo followed by purification by flash column chromatography (Merck silica gel 60, 40-63 μm; 25% ethyl acetate/hexanes to 70% ethyl acetate/hexanes) afforded 1-propyl-1H-pyrazol-3-ylamine (54 mg, 73%) as a golden oil: ESI-LRMS m/e calcd for C6H11N3 [M+] 125.10, found 126.3 [M+H+], 251.3 [2M+H+].

Workup

  1. concentrationconcentrated in vacuo
  2. customfollowed by purification by flash column chromatography (Merck silica gel 60, 40-63 μm; 25% ethyl acetate/hexanes to 70% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-b1f83c1cda04427e884b2859b95751d0
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

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