N-Methyl-6-nitro-N-[(4-nitrophenoxy)propyl]-2-quinoline-methanamine → 6-Amino-N-[(4-aminophenoxy)propyl]-N-methyl-2-quinoline methanamine

HRID 1091097Notes

Reaction equation

HRID 1091097 reaction equation
[CH3:1][N:2]([CH2:17][CH2:18][CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][CH:22]=1)[CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:14]([O-])=O)[CH:10]=2)[N:5]=1>C(O)C.O=[Pt]=O>[NH2:14][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[C:4]([CH2:3][N:2]([CH2:17][CH2:18][CH2:19][O:20][C:21]1[CH:22]=[CH:23][C:24]([NH2:27])=[CH:25][CH:26]=1)[CH3:1])[CH:13]=[CH:12]2

Participants

4

Reactant 1

HCID 15675923N-Methyl-6-nitro-N-[(4-nitrophenoxy)propyl]-2-quinoline-methanamine

Product 1

HCID 156759246-Amino-N-[(4-aminophenoxy)propyl]-N-methyl-2-quinoline methanamineYield 98.6%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

N-Methyl-6-nitro-N-[(4-nitrophenoxy)propyl]-2-quinoline methanamine (2.60 g, 6.57 mmol) was dissolved in ethanol (170 mL) containing PtO2 (0.39 g). The mixture was charged with H2 (g) (1 atm), stirred for 4 hours, and filtered through a pad of solka floc. The filtrate was concentrated to afford 2.18 g of product as a yellow oil that was used directly without purification.

Workup

  1. additionThe mixture was charged with H2 (g) (1 atm)
  2. filtrationfiltered through a pad of solka floc
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-0aa05394e292401c83cc1f0d7edb2be6
Source dataset
uspto-grants-1992_01
Patent number
US05084463

Reaction notes

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