5-(2-Methoxy-5-nitrophenyl)-1-methyl-1H-pyrazole → 4-methoxy-3-(2-methyl-2H-pyrazol-3-yl)phenylamine

HRID 1626180Notes

Reaction equation

HRID 1626180 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[CH:5][C:4]=1[C:12]1[N:16]([CH3:17])[N:15]=[CH:14][CH:13]=1>C(O)(=O)C.[Zn]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][C:4]=1[C:12]1[N:16]([CH3:17])[N:15]=[CH:14][CH:13]=1

Participants

4

Reactant 1

HCID 231395315-(2-Methoxy-5-nitrophenyl)-1-methyl-1H-pyrazole

Product 1

HCID 231394504-methoxy-3-(2-methyl-2H-pyrazol-3-yl)phenylamineYield 62.8%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 5-(2-methoxy-5-nitro-phenyl)-1-methyl-1H-pyrazole (7.95 g, 34.1 mmol) in acetic acid (250 mL) was added zinc dust (11.7 g, 179 mmol) in portions under cooling in an ice bath over a period of 10 minutes. After stirring for 30 min at room temperature, solids were filtered of through celite. Filtrate was concentrated and residue was purified by SiO2 column chromatography (Eluent: methylene chloride/methanol 20: 1) to give 4-methoxy-3-(2-methyl-2H-pyrazol-3-yl)-phenylamine (4.34 g, 21.4 mmol, 62%) as an oil. LCMS m/z (%)=204 (M+H). 1H NMR (400 MHz, CDCl3) δ: 7.51 (d, J=1.8 Hz, 1H), 6.83 (d, J=8.7 Hz, 1H), 6.76 (dd, J=2.8, 8.7 Hz, 1H), 6.62 (d, J=2.8 Hz, 1H), 6.22 (d, J=1.8 Hz, 1H), 3.74 (s, 3H), 3.73 (s, 3H), 3.24-3.55 (broad s, 2H).

Workup

  1. temperatureunder cooling in an ice bath over a period of 10 minutes
  2. filtrationsolids were filtered of through celite
  3. concentrationFiltrate was concentrated
  4. customresidue was purified by SiO2 column chromatography (Eluent: methylene chloride/methanol 20: 1)

Sources & evidence

ORD record
ord-8048b973aaa640f6881db2163ed54646
Source dataset
uspto-grants-2014_07
Patent number
US08785441B2

Reaction notes

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