4-Nitro-1-(2-pyrrolidin-1-yl-ethyl)-1H-pyrazole → 1-(2-(pyrrolidin-1-yl)ethyl)-1H-pyrazol-4-amine

HRID 472525Notes

Reaction equation

HRID 472525 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][N:7]([CH2:9][CH2:10][N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:8]=1)([O-])=O>[Pd].C(O)C>[N:11]1([CH2:10][CH2:9][N:7]2[CH:8]=[C:4]([NH2:1])[CH:5]=[N:6]2)[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

4

Reactant 1

HCID 674814064-Nitro-1-(2-pyrrolidin-1-yl-ethyl)-1H-pyrazole

Product 1

HCID 621376891-(2-(pyrrolidin-1-yl)ethyl)-1H-pyrazol-4-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-nitro-1-(2-pyrrolidin-1-yl-ethyl)-1H-pyrazole (4.40 g, 20.9 mmol), ethanol (100 mL) and 10% palladium on carbon (0.41 g, 30.7 mmol) was hydrogenated in a Paar shaker at 30 psi under hydrogen for 2 h. The reaction mixture was filtered over diatomaceous earth and the filtrate was evaporated in vacuo. 1-(2-Pyrrolidin-1-yl-ethyl)-1H-pyrazol-4-ylamine was isolated as an orange oil, which became a dark gummy material upon standing at room temperature (3.10 g, 82%). 1H NMR (400 MHz, CDCl3, δ, ppm): 7.15 (s, 1H), 7.08 (s, 1H), 4.14 (t, J=7.00 Hz, 2H), 2.88 (t, J=6.97 Hz, 4H), 2.52 (s, 4H), 1.765 (s, 4H). MS=181 (MH)+.

Workup

  1. filtrationThe reaction mixture was filtered over diatomaceous earth
  2. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-c2bab19135f649c7b9b1411f1042c453
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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