HCID 973664, compound → HCID 7148582, compound

HRID 1508879Notes

Reaction equation

HRID 1508879 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][N:5]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=2)[CH:6]=1>C(OCC)(=O)C.[Pt]>[Cl:1][C:2]1[CH:3]=[N:4][N:5]([CH2:7][C:8]2[CH:9]=[CH:10][C:11]([NH2:14])=[CH:12][CH:13]=2)[CH:6]=1

Participants

4

Reactant 1

HCID 973664HCID 973664, compound

Product 1

HCID 7148582HCID 7148582, compoundYield 54.4%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-chloro-1-(4-nitrobenzyl)-1H-pyrazole (0.750 g, 3.16 mmol) in ethyl acetate (30 mL) was added Pt/C (0.038 g, 0.19 mmol). The mixture was stirred at rt for 48 h, filtered through celite, washed with ethyl acetate, and the filtrate was concentrated. The residue was purified by column chromatography (silica, hexanes/ethyl acetate) to afford the title compound (0.357 g, 43%) as a peach solid. MW=207.66. 1H NMR (CDCl3, 500 MHz) δ 7.41 (s, 1H), 7.26 (s, 1H), 7.07-7.01 (m, 2H), 6.65-6.59 (m, 2H), 5.09 (s, 2H), 3.74 (s, 2H); APCI MS m/z 207 [M+H]+.

Workup

  1. filtrationfiltered through celite
  2. washwashed with ethyl acetate
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by column chromatography (silica, hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-751f3e9587c741688a6f9d0fad5bd85e
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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