5-(methoxymethyl)-1-methyl-3-nitro-1H-pyrazole → 5-(Methoxymethyl)-1-methyl-1H-pyrazol-3-amine

HRID 1022251Notes

Reaction equation

HRID 1022251 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[N:8]([CH3:9])[N:7]=[C:6]([N+:10]([O-])=O)[CH:5]=1>[Pd].C(O)C>[CH3:1][O:2][CH2:3][C:4]1[N:8]([CH3:9])[N:7]=[C:6]([NH2:10])[CH:5]=1

Participants

4

Reactant 1

HCID 580442075-(methoxymethyl)-1-methyl-3-nitro-1H-pyrazole

Product 1

HCID 580437775-(Methoxymethyl)-1-methyl-1H-pyrazol-3-amineYield 101.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer was charged with 336a (4.0 g, 23 mmol), Pd/C (1.0 g), and ethanol (100 mL). The mixture was hydrogenated at room temperature for 15 h. It was then filtered and the filtrate was concentrated under reduced pressure to afford 336b as a yellow oil (3.3 g, 99%), which was used in the next step without further purification. MS-ESI: [M+H]+ 142.

Workup

  1. customA 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. filtrationIt was then filtered
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7786445e09704529b61393aedbbe9ad8
Source dataset
uspto-grants-2014_05
Patent number
US08716274B2

Reaction notes

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