3-(4-Methylpiperazin-1-yl)-2-nitroaniline → 3-(4-Methylpiperazin-1-yl)benzene-1,2-diamine

HRID 470343Notes

Reaction equation

HRID 470343 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:9]([N+:15]([O-])=O)=[C:10]([NH2:14])[CH:11]=[CH:12][CH:13]=2)[CH2:4][CH2:3]1>CO.[Pd]>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([NH2:14])[C:9]=2[NH2:15])[CH2:6][CH2:7]1

Participants

4

Reactant 1

HCID 461799823-(4-Methylpiperazin-1-yl)-2-nitroaniline

Product 1

HCID 218773413-(4-Methylpiperazin-1-yl)benzene-1,2-diamineYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-(4-methyl-piperazin-1-yl)-2-nitro-phenylamine (139 mg, 0.59 mmol) in MeOH (20 mL) were added Pd/C (10%, 14 mg) and the mixture was stirred under atmospheric hydrogen (balloon) at the room temperature for 1 h. The reaction mixture was filter over Celite to afford the title compound (120 mg, 99%). 1H NMR (MeOH-d4) δ 2.34 (s, 3H), 2.62 (br, 4H), 2.99 (m, 4H), 6.51-6.65 (3H). ESI-MS m/z 207.1 (MH+).

Workup

  1. filtrationThe reaction mixture was filter over Celite

Sources & evidence

ORD record
ord-1913e753ba934e0a8d9608ea55b5a22b
Source dataset
uspto-grants-2014_01
Patent number
US08629147B2

Reaction notes

Loading…