3-Nitro-1-(2-phenylethyl)-1H-pyrazole → HCID 58710072, compound

HRID 2375848Notes

Reaction equation

HRID 2375848 reaction equation
[N+:1]([C:4]1[CH:8]=[CH:7][N:6]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:5]=1)([O-])=O>C(OCC)(=O)C.C(O)C.[Pd]>[NH2:1][C:4]1[CH:8]=[CH:7][N:6]([CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:5]=1

Participants

5

Reactant 1

HCID 587099233-Nitro-1-(2-phenylethyl)-1H-pyrazole

Product 1

HCID 58710072HCID 58710072, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-nitro-1-phenethyl-1H-pyrazole (90 mg, 0.41 mmol) in ethyl acetate (2 mL) and ethanol (2 mL) was added 10% Pd—C (20 mg), the resulting mixture was stirred under hydrogen atmosphere overnight. TLC showed the reaction was complete. The catalyst was removed by filtration through a pad of celite, and the filtrate was concentrated under reduced pressure to give the title compound as colorless oil. LC-MS (ES, Pos.): 188 [MH+]. 1H NMR (CDCl3, 400 MHz): δ=3.10 (t, J=7.2 Hz, 2H), 3.64 (br s, 2H), 4.12 (t, J=7.2 Hz, 2H), 5.51 (d, J=2.3 Hz, 1H), 6.91 (d, J=2.3 Hz, 1H), 7.08-7.11 (m, 2H), 7.20-7.30 (m, 3H).

Workup

  1. customThe catalyst was removed by filtration through a pad of celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a2560a1aaa7b4796a614512b73a9cbdb
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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