4-(2-methoxy-4-nitrophenyl)-1-methyl-1H-pyrazole → 3-methoxy-4-(1-methyl-1H-pyrazol-4-yl)aniline

HRID 1855510Notes

Reaction equation

HRID 1855510 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[C:12]1[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=1.[H][H]>[Pd].CO>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([NH2:9])[CH:6]=[CH:5][C:4]=1[C:12]1[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=1

Participants

5

Reactant 2

HCID 668604724-(2-methoxy-4-nitrophenyl)-1-methyl-1H-pyrazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 584144723-methoxy-4-(1-methyl-1H-pyrazol-4-yl)anilineYield 100.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-(2-methoxy-4-nitro-phenyl)-1-methyl-1H-pyrazole (240 mg, 1.03 mmol) and palladium on carbon 10% (55 mg, 0.052 mmol) in methanol (15 mL) was stirred for 2 hours at under hydrogen atmosphere. The mixture was filtrated and the solvent evaporated to afford the title compound (210 mg, 100%) as a white solid. MS ISP (m/e): 204.3.0 [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.76 (s, 1H), 7.70 (s, 1H), 7.28 (d, 1H), 6.32 (d, 2H), 3.91 (s, 3H), 3.85 (s, 3H), 3.68 (s broad, 2H). Mp 129-131° C.

Workup

  1. filtrationThe mixture was filtrated
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-9df6a4563e6e49baa2dd7041b5090aae
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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