1-(3-methoxy-4-nitro-1H-pyrazol-1-yl)propan-2-ol → 1-(3-methoxy-4-amino-1H-pyrazol-1-yl)propan-2-ol

HRID 928215Notes

Reaction equation

HRID 928215 reaction equation
[CH3:1][O:2][C:3]1[C:7]([N+:8]([O-])=O)=[CH:6][N:5]([CH2:11][CH:12]([OH:14])[CH3:13])[N:4]=1>[Pd].CO>[CH3:1][O:2][C:3]1[C:7]([NH2:8])=[CH:6][N:5]([CH2:11][CH:12]([OH:14])[CH3:13])[N:4]=1

Participants

4

Reactant 1

HCID 1180737151-(3-methoxy-4-nitro-1H-pyrazol-1-yl)propan-2-ol

Product 1

HCID 1180735971-(3-methoxy-4-amino-1H-pyrazol-1-yl)propan-2-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A nitrogen-flushed round bottom flask was charged with 1-(3-methoxy-4-nitro-1H-pyrazol-1-yl)propan-2-ol (345 mg, 1.72 mmol, 1.00 eq), 10% Pd/C (200 mg) and methanol (20 mL). The reaction mixture was sparged with hydrogen for 10 min then stirred vigorously under hydrogen atmosphere for 14 hr. The reaction mixture was then sparged with nitrogen, filtered through Celite®, and concentrated to give the title compound as an oil that was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 6.92 (s, 1H) 4.70 (d, J=4.9 Hz, 1H) 3.89-3.77 (m, 1H) 3.74 (s, 3H) 3.73-3.55 (m, 2H) 0.97 (d, J=6.2 Hz, 3H). m/z (APCI+) for C7H14N3O2 172.3 (M+H)+.

Workup

  1. customA nitrogen-flushed round bottom flask
  2. customThe reaction mixture was sparged with hydrogen for 10 min
  3. customThe reaction mixture was then sparged with nitrogen
  4. filtrationfiltered through Celite®
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-48c45d036ee8453babc0a444b33f4320
Source dataset
uspto-grants-2016_03
Patent number
US09290496B2

Reaction notes

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