1-(2-isopropoxy-ethyl)-3-nitro-1H-pyrazole → HCID 61485333, compound

HRID 546192Notes

Reaction equation

HRID 546192 reaction equation
[CH:1]([O:4][CH2:5][CH2:6][N:7]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[N:8]1)([CH3:3])[CH3:2].[H][H]>[Pd].C(O)C>[CH:1]([O:4][CH2:5][CH2:6][N:7]1[CH:11]=[CH:10][C:9]([NH2:12])=[N:8]1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 671901471-(2-isopropoxy-ethyl)-3-nitro-1H-pyrazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 61485333HCID 61485333, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In a Parr shaker bottle was placed 1-(2-isopropoxy-ethyl)-3-nitro-1H-pyrazole (428 mg, 2.14 mmol), 10% palladium on activated carbon (50 mg) and ethanol (20 mL). The bottle was then placed on the Parr shaker at 50 psi of hydrogen pressure for 2 h. The reaction was then filtered through a pad of celite and washed with ethanol, concentration in vacuo afforded 1-(2-isopropoxy-ethyl)-1H-pyrazol-3-ylamine (360 mg, 99%) as a clear light yellow oil: ES-HRMS m/e calcd for C8H15N3 (M+H)+ 170.1288, observed 170.1287; 1H NMR (300 MHz, CDCl3) δ 1.10 (d, J=6.0 Hz, 6H, 2×CH3), 3.43 (br, 2 H, NH2), 3.49 (m, 1H, OCH), 3.70 (t, J=5.6 Hz, 2H, OCH2), 4.05 (t, J=5.6 Hz, 2H, NCH2), 5.57 (d, J=2.3 Hz, 1H, Ar), 7.22 (d, J=2.3 Hz, 1H, Ar).

Workup

  1. filtrationThe reaction was then filtered through a pad of celite
  2. washwashed with ethanol, concentration in vacuo

Sources & evidence

ORD record
ord-644cb7b3dff44732b98f791c728a3d08
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

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