N-[4-[2-Hydroxy-3-[methyl[(6-nitro-2-quinolinyl)methyl]amino]propoxy]phenyl]methanesulfonamide → N-[4-[3-[[(6-Amino-2-quinolinyl)methyl]methylamino]-2-hydroxypropoxy] phenyl]methanesulfonamide

HRID 1091090Notes

Reaction equation

HRID 1091090 reaction equation
[OH:1][CH:2]([CH2:16][N:17]([CH3:32])[CH2:18][C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[C:24]([N+:29]([O-])=O)[CH:25]=2)[N:20]=1)[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[CH:7][CH:6]=1>C(O)C.O=[Pt]=O>[NH2:29][C:24]1[CH:25]=[C:26]2[C:21](=[CH:22][CH:23]=1)[N:20]=[C:19]([CH2:18][N:17]([CH3:32])[CH2:16][CH:2]([OH:1])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[CH:7][CH:6]=1)[CH:28]=[CH:27]2

Participants

4

Reactant 1

HCID 15675910N-[4-[2-Hydroxy-3-[methyl[(6-nitro-2-quinolinyl)methyl]amino]propoxy]phenyl]methanesulfonamide

Product 1

HCID 15675911N-[4-[3-[[(6-Amino-2-quinolinyl)methyl]methylamino]-2-hydroxypropoxy] phenyl]methanesulfonamideYield 89%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

N-[4-[2-Hydroxy-3-[methyl[(6-nitro-2-quinolinyl)methyl]amino]propoxy]phenyl]methanesulfonamide (1.20 g, 2.61 mmol) and PtO2 (0.120 g, 10% by wt.) were suspended in ethanol (100 mL) and the flask was charged with H2 (1 atm). After stirring for 6 hours, the mixture was filtered through a pad of solka floc and the filtrate was concentrated in vacuo to afford 1.00 g of product as a pale oil which was used directly in the next step.

Workup

  1. additionthe flask was charged with H2 (1 atm)
  2. filtrationthe mixture was filtered through a pad of solka floc
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-0e1bc9f8d1da410195f9c0d913604234
Source dataset
uspto-grants-1992_01
Patent number
US05084463

Reaction notes

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