Ethyl Acetate → 3-(methoxymethyl)-1-methyl-1H-pyrazol-4-amine

HRID 1045963Notes

Reaction equation

HRID 1045963 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[C:8]([N+:9]([O-])=O)=[CH:7][N:6]([CH3:12])[N:5]=1.CCOC(C)=O>CO.[Pd]>[CH3:1][O:2][CH2:3][C:4]1[C:8]([NH2:9])=[CH:7][N:6]([CH3:12])[N:5]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 673085153-(Methoxymethyl)-1-methyl-4-nitropyrazole

Product 1

HCID 552845543-(methoxymethyl)-1-methyl-1H-pyrazol-4-amineYield 70.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% wt Pd/C (50% wet) (2 g) was added to a stirred solution of 3-(methoxymethyl)-1-methyl-4-nitropyrazole (2.02 g) in MeOH (60 ml) and the mixture stirred under an atmosphere of hydrogen overnight. The reaction mixture was filtered through a plug of celite, and the cake washed with EtOAc (200 ml). The volatiles were removed under reduced pressure to give the crude product as a brown oil. Subsequent column chromatography (SiO2; 100% EtOAc) of the crude material gave 3-(methoxymethyl)-1-methylpyrazol-4-amine (1.18 g, 70%) as a brown liquid. NMR Spectrum: (CDCl3) 2.9 (m, 2H), 3.35 (s, 3H), 3.74 (s, 3H), 4.46 (s, 2H), 6.91 (s, 1H)

Workup

  1. filtrationThe reaction mixture was filtered through a plug of celite
  2. washthe cake washed with EtOAc (200 ml)
  3. customThe volatiles were removed under reduced pressure
  4. customto give the crude product as a brown oil

Sources & evidence

ORD record
ord-0ba88472d669466ca25ceb14b9c9459e
Source dataset
uspto-grants-2013_10
Patent number
US08569298B2

Reaction notes

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