(2-Nitrophenyl)-(1,3,5-trimethyl-1H-pyrazol-4-yl)-amine → N-(1,3,5-Trimethyl-1H-pyrazol-4-yl)-benzene-1,2-diamine

HRID 1599082Notes

Reaction equation

HRID 1599082 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]1[C:12]([CH3:18])=[N:13][N:14]([CH3:17])[C:15]=1[CH3:16])([O-])=O>C(OCC)(=O)C.[Pd]>[CH3:17][N:14]1[C:15]([CH3:16])=[C:11]([NH:10][C:5]2[C:4]([NH2:1])=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:12]([CH3:18])=[N:13]1

Participants

4

Reactant 1

HCID 18929580(2-Nitrophenyl)-(1,3,5-trimethyl-1H-pyrazol-4-yl)-amine

Product 1

HCID 18929578N-(1,3,5-Trimethyl-1H-pyrazol-4-yl)-benzene-1,2-diamineYield 99.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2-Nitro-phenyl)-(1,3,5-trimethyl-1H-pyrazol-4-yl)-amine (8.6 g, 35 mmol) in ethyl acetate (175 mL) was added 10% palladium on carbon (1 g). The solution was stirred under a hydrogen atmosphere (50 psi) for 15 h and subsequently filtered through a bed of celite, washed with ethyl acetate, and concentrated in vacuo to yield the title compound (7.56 g): 1HNMR (CDCl3, 300 MHz) δ 6.74 (m, 3H), 6.32 (d, 1H, J=1.9, 7.2), 4.6 (s, 1H), 3.75 (s, 3H), 3.1 (s, 2H), 2.05 (m, 6H); low resolution MS(FAB) m/z 217 (MH+).

Workup

  1. filtrationsubsequently filtered through a bed of celite
  2. washwashed with ethyl acetate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e4e83fb4b1b04a4da0dd2e8d6611240c
Source dataset
uspto-grants-1998_04
Patent number
US05739129

Reaction notes

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