1-(4-Methoxybenzyl)-4-nitro-1H-pyrazole → 1-((4-methoxyphenyl)methyl)-1H-pyrazol-4-amine

HRID 1812157Notes

Reaction equation

HRID 1812157 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([N+:13]([O-])=O)[CH:10]=[N:9]2)=[CH:5][CH:4]=1>CCO.[NH4+].[Cl-].CCOC(C)=O.[Fe]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([NH2:13])[CH:10]=[N:9]2)=[CH:16][CH:17]=1

Participants

6

Reactant 1

HCID 666114661-(4-Methoxybenzyl)-4-nitro-1H-pyrazole

Product 1

HCID 283739871-((4-methoxyphenyl)methyl)-1H-pyrazol-4-amineYield 62.4%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
105 °C

Procedure

A solution of 1-(4-methoxybenzyl)-4-nitro-1H-pyrazole (1031 mg, 4.42 mmol) in EtOH (25 mL) and sat. aq. NH4Cl (15 mL) in a sealed tube (125 mL) was treated with iron (1234 mg, 22.10 mmol, Aldrich, St. Louis, Mo.). The mixture was stirred at 105° C. for 1 h, then cooled to room temperature. The mixture was diluted with EtOAc (200 mL) and filtered through a plug of Celite® (diatomaceous earth). The filtrate was separated and the organic layer was dried (MgSO4), filtered and concentrated in vacuo. The residue was filtered through a plug of silica gel (eluting with DCM:EtOAc: MeOH=25:25:1) to give 1-(4-methoxybenzyl)-1H-pyrazol-4-amine (560 mg, 2.76 mmol, 62.3% yield) as a brown solid. m/z (ESI, positive ion) 204 (M+H)+.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered through a plug of Celite® (diatomaceous earth)
  3. customThe filtrate was separated
  4. dry with materialthe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. filtrationThe residue was filtered through a plug of silica gel (eluting with DCM:EtOAc: MeOH=25:25:1)

Sources & evidence

ORD record
ord-582f554aba5a4270bb963e1b3366b6db
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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