Methyl 1-methyl-4-nitro-1H-pyrazole-3-carboxylate → methyl 4-amino-1-methyl-1H-pyrazole-3-carboxylate

HRID 720685Notes

Reaction equation

HRID 720685 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:9]([N+:10]([O-])=O)=[CH:8][N:7]([CH3:13])[N:6]=1)=[O:4].[H][H]>[Pd].CO>[CH3:1][O:2][C:3]([C:5]1[C:9]([NH2:10])=[CH:8][N:7]([CH3:13])[N:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 54775322Methyl 1-methyl-4-nitro-1H-pyrazole-3-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 7017722methyl 4-amino-1-methyl-1H-pyrazole-3-carboxylateYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-methyl-4-nitro-1H-pyrazole-3-carboxylic acid methyl ester (500 mg, 2.7 mmol) and 10% palladium on carbon (50 mg) in methanol (25 mL) was subjected to 60 psi pressure of hydrogen gas in a Parr apparatus for 24 h. At this time, the reaction mixture was filtered through a pad of celite and washed with methanol. The filtrate was concentrated in vacuo to afford 4-amino-1-methyl-1H-pyrazole-3-carboxylic acid methyl ester (402 mg, 96%) as an off-white solid: 1H NMR (DMSO-d6, 300 MHz) δ7.10 (s, 1H), 4.65 (broad s, 2H), 3.73 (s, 3H), 3.72 (s, 3H).

Workup

  1. filtrationAt this time, the reaction mixture was filtered through a pad of celite
  2. washwashed with methanol
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-d8cb0ed77f5740d5a4726e31e0966c3b
Source dataset
uspto-grants-2006_11
Patent number
US07135475B2

Reaction notes

Loading…