2-Methoxy-4-(3-(methylsulfonyl)propoxy)-1-nitrobenzene → 4-(3-Methanesulfonyl-propoxy)-2-methoxy-phenylamine

HRID 417340Notes

Reaction equation

HRID 417340 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH2:10][CH2:11][CH2:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH:6]=[CH:5][C:4]=1[N+:17]([O-])=O>CO.[Pd]>[CH3:16][S:13]([CH2:12][CH2:11][CH2:10][O:9][C:7]1[CH:6]=[CH:5][C:4]([NH2:17])=[C:3]([O:2][CH3:1])[CH:8]=1)(=[O:14])=[O:15]

Participants

4

Reactant 1

HCID 666252522-Methoxy-4-(3-(methylsulfonyl)propoxy)-1-nitrobenzene

Product 1

HCID 582862934-(3-Methanesulfonyl-propoxy)-2-methoxy-phenylamineYield 115.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Step C A suspension of 2-methoxy-4-(3-(methylsulfonyl)propoxy)-1-nitrobenzene (0.4 g, 1.6 mmol) and Pd/C (Aldrich, 10%, 0.1 g) in methanol (15 mL) was vigorously shaken in a Parr under atmosphere of H2 (50 psi) for 0.5 h. The mixture was filtered through a short pad of celite. The filtrate was concentrated to give 4-(3-methanesulfonyl-propoxy)-2-methoxy-phenylamine as a black oil (0.48 g, 92%).

Workup

  1. filtrationThe mixture was filtered through a short pad of celite
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-78f0486ef7a64878962db00d225ac371
Source dataset
uspto-grants-2012_01
Patent number
US08088815B2

Reaction notes

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