HCID 67374679, compound → HCID 61368793, compound

HRID 515792Notes

Reaction equation

HRID 515792 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-])=O>CCO.[Pd]>[N:18]1[CH:19]=[CH:20][C:15]([CH2:14][CH2:13][S:10]([C:7]2[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)(=[O:12])=[O:11])=[CH:16][CH:17]=1

Participants

4

Reactant 1

HCID 67374679HCID 67374679, compound

Product 1

HCID 61368793HCID 61368793, compoundYield 50.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-(2-((4-nitrophenyl)sulfonyl)ethyl)pyridine (210 mg, 0.76 mmol) and 10% Pd/C (100 mg) in EtOH (100 mL) was stirred at room temperature for 3 h under H2 atmosphere (balloon). The reaction mixture was filtered and the filtrate was concentrated to dryness. The residue was purified by column chromatography on silica gel (MeOH/DCM=1/50) to afford 100 mg of 4-((2-(pyridin-4-yl)ethyl)sulfonyl)aniline as a white solid. 1H NMR (300 MHz, CDCl3) δ 8.48 (m, 2H), 7.67 (m, 2H), 7.05 (m, 2H), 6.70 (m, 2H), 4.23 (bs, 2H), 3.34-3.28 (m, 2H), 3.07-3.01 (m, 2H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated to dryness
  3. customThe residue was purified by column chromatography on silica gel (MeOH/DCM=1/50)

Sources & evidence

ORD record
ord-00f6895730c04605821c9453797d90ff
Source dataset
uspto-grants-2015_08
Patent number
US09108944B2

Reaction notes

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