3-(4-Nitro-1H-pyrazol-1-yl)pyridine → Pyridine, 3-(4-aminopyrazol-1-yl)-

HRID 2408173Notes

Reaction equation

HRID 2408173 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][N:7]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:8]=1)([O-])=O>C1COCC1.[Pd]>[N:11]1[CH:12]=[CH:13][CH:14]=[C:9]([N:7]2[CH:8]=[C:4]([NH2:1])[CH:5]=[N:6]2)[CH:10]=1

Participants

4

Reactant 1

HCID 126612223-(4-Nitro-1H-pyrazol-1-yl)pyridine

Product 1

HCID 206682Pyridine, 3-(4-aminopyrazol-1-yl)-Yield 122.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(4-nitro-pyrazol-1-yl)-pyridine (1.8 g, 0.009 mol) in dry THF (18 ml) was added 5% Pd/C (180 mg) under nitrogen atmosphere. The mixture was then stirred under hydrogen atmosphere until the reaction was complete. The reaction mixture was filtered through a pad of celite, and concentrated to dryness to give an impure dark brown solid (1.76 g): 1H NMR (400 MHz, DMSO-d6) δ 8.89 (dd, J=2.8. 0.4 Hz, 1H); 8.48 (dd, J=4.8, 1.2 Hz, 1H), 7.99-7.96 (m, 1H), 7.54 (d, J=1.2 Hz, 1H), 7.45 (d, J=0.4 Hz, 1H), 7.38-7.35 (m, 1H), 4.81 (bs 1H); ESIMS (m/z) 161 [M+1].

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-dcc370cacda344feb5c32c88b89ec5f6
Source dataset
uspto-grants-2014_08
Patent number
US08815271B2

Reaction notes

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