HCID 59349549, compound → HCID 59349505, compound

HRID 415122Notes

Reaction equation

HRID 415122 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:18]=[CH:17][C:15]([NH2:16])=[C:14]([N+:19]([O-])=O)[CH:13]=2)[CH2:4][CH2:3]1>[Pd].C(O)C>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:13]=[C:14]([NH2:19])[C:15]([NH2:16])=[CH:17][CH:18]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 59349549HCID 59349549, compound

Product 1

HCID 59349505HCID 59349505, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A hydrogenation vessel was charged with 4-(3-(4-methylpiperazin-1-yl)propoxy)-2-nitroaniline (1.4 g, 4.76 mmol), ethanol (100 mL) and 10% palladium on charcoal (1 g). The reaction vessel was shaken on Parr hydrogenation apparatus. After 2 hours, the reaction mixture was filtered through a plug of Celite and washed with methanol. The resulting filtrate was concentrated under reduced pressure to 1.2 g of 4-(3-(4-methylpiperazin-1-yl)propoxy)benzene-1,2-diamine (95% yield), and was used without any further purification. MS (EI: 265 (MH+).

Workup

  1. filtrationthe reaction mixture was filtered through a plug of Celite
  2. washwashed with methanol

Sources & evidence

ORD record
ord-ad6fd48d630645e6b64ce299c1051dca
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

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