2-(4-nitro-1H-pyrazol-1-yl)-N-(propan-2-yl)acetamide → 2-(4-amino-1H-pyrazol-1-yl)-N-isopropylacetamide

HRID 929921Notes

Reaction equation

HRID 929921 reaction equation
[CH:1]([NH:4][C:5](=[O:15])[CH2:6][N:7]1[CH:11]=[C:10]([N+:12]([O-])=O)[CH:9]=[N:8]1)([CH3:3])[CH3:2]>C1COCC1.[Pd]>[NH2:12][C:10]1[CH:9]=[N:8][N:7]([CH2:6][C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[O:15])[CH:11]=1

Participants

4

Reactant 1

HCID 15046362-(4-nitro-1H-pyrazol-1-yl)-N-(propan-2-yl)acetamide

Product 1

HCID 283739432-(4-amino-1H-pyrazol-1-yl)-N-isopropylacetamideYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N-isopropyl-2-(4-nitro-1H-pyrazol-1-yl)acetamide (12 g, 56.5 mmol) and Pd/C (1 g) in THF (100 mL) was stirred at room temperature under an atmosphere of hydrogen for 5 h then filtered over Celite. The filtrate was concentrated in vacuo to afford 2-(4-amino-1H-pyrazol-1-yl)-N-isopropylacetamide V-3 (10.3 g, 100%). LC-MS (Method A), RT=1.42 min. (ES+) 183.

Workup

  1. filtrationthen filtered over Celite
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-cdcc790b19e5486baa2d4f14b17c0e3f
Source dataset
uspto-grants-2016_03
Patent number
US09296725B2

Reaction notes

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