HCID 66637154, compound → HCID 66637050, compound

HRID 1094636Notes

Reaction equation

HRID 1094636 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:10][S:11]([C:13]([CH3:16])([CH3:15])[CH3:14])=[O:12])[CH3:9])=[CH:4][C:3]=1[N+:17]([O-])=O>CCO.[C].[Pd]>[NH2:17][C:3]1[CH:4]=[C:5]([CH:8]([NH:10][S:11]([C:13]([CH3:14])([CH3:16])[CH3:15])=[O:12])[CH3:9])[CH:6]=[CH:7][C:2]=1[NH2:1]

Participants

4

Reactant 1

HCID 66637154HCID 66637154, compound

Product 1

HCID 66637050HCID 66637050, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of N-[1-(4-amino-3-nitrophenyl)ethyl]-2-methylpropane-2-sulfinamide (670 mg, 2.35 mmol) and 10% palladium-carbon (70 mg) in EtOH (50 ml) was stirred under hydrogen (4 atm) at room temperature for 6 hours. The mixture was filtered through a pad of Celite. The filtrate was concentrated to give 598 mg of the title compound as a brown solid. 1H NMR (300 MHz, CDCl3) δ ppm 1.22 (9H, s), 1.45 (3H, d, J=6.6 Hz), 3.50-3.32 (4H, m), 4.45-4.37 (1H, m), 6.71-6.65 (3H, m). A signal due to NH was not observed. MS (ESI) m/z 256 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-515ccd7a17b1432a9a59b6aac2874c10
Source dataset
uspto-grants-2012_03
Patent number
US08134004B2

Reaction notes

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