Methanol → 5'-Amino-2'-[2-(isopropylamino)ethoxy]methanesulfonanilide

HRID 379714Notes

Reaction equation

HRID 379714 reaction equation
[CH:1]([NH:4][CH2:5][CH2:6][O:7][C:8]1[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][C:9]=1[NH:10][S:11]([CH3:14])(=[O:13])=[O:12])([CH3:3])[CH3:2].CO>[C].[Pd].C(OCC)(=O)C>[NH2:19][C:16]1[CH:17]=[CH:18][C:8]([O:7][CH2:6][CH2:5][NH:4][CH:1]([CH3:3])[CH3:2])=[C:9]([CH:15]=1)[NH:10][S:11]([CH3:14])(=[O:13])=[O:12]

Participants

5

Reactant 2

HCID 887MethanolHCID 183682892'-[2-(Isopropylamino)ethoxy]-5'-nitromethanesulfonanilide

Product 1

HCID 183683615'-Amino-2'-[2-(isopropylamino)ethoxy]methanesulfonanilideYield 93.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2′-[2-(Isopropylamino)ethoxy]-5′-nitromethanesulfonanilide (26.1 g) was dissolved into mixed solvents of methanol (200 ml) and ethyl acetate (200 ml) and subjected to hydrogenation reaction with 10% palladium carbon catalyst at ambient pressure. After completion of hydrogenation reaction, catalyst was removed by filtration. Filtrate was concentrated to dryness under vacuum to obtain 5′-amino-2′-[2-(isopropylamino)ethoxy]methanesulfonanilide (22 g) as brownish solid.

Workup

  1. customAfter completion of hydrogenation reaction, catalyst
  2. customwas removed by filtration
  3. concentrationFiltrate was concentrated to dryness under vacuum

Sources & evidence

ORD record
ord-ff151eb6ebfb439f85cc9c12f0d2c1cf
Source dataset
uspto-grants-2001_10
Patent number
US06300368B1

Reaction notes

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