1-(3,5-Dioxapiperidin-1-yl)sulphonyl-4-nitrobenzene → 4-(3,5-Dioxapiperidin-1-yl)sulphonylaniline

HRID 23918Notes

Reaction equation

HRID 23918 reaction equation
[N:1]1([S:7]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH2:6][O:5][CH2:4][O:3][CH2:2]1>[Pd].C(O)C.C(OCC)(=O)C>[N:1]1([S:7]([C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2)(=[O:8])=[O:9])[CH2:2][O:3][CH2:4][O:5][CH2:6]1

Participants

5

Reactant 1

HCID 220249211-(3,5-Dioxapiperidin-1-yl)sulphonyl-4-nitrobenzene

Product 1

HCID 225702274-(3,5-Dioxapiperidin-1-yl)sulphonylanilineYield 88.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-(3,5-dioxapiperidin-1-yl)sulphonyl-4-nitrobenzene (Method 8) (500 mg, 1.82 mmol) and 10% palladium on charcoal catalyst (150 mg) in ethanol (25 ml) and ethyl acetate (25 ml) was stirred under an atmosphere of hydrogen for 3 hours. The catalyst was removed by filtration through diatomaceous earth and the filter pad was washed with ethanol and ethyl acetate. The volatiles were removed from the filtrate by evaporation and the residue triturated with ether and hexane to give the tide compound (395 mg, 88%). NMR: 4.90 (s, 2H) 5.10 (s, 4H), 6.02 (s, 2H), 6.58 (d, 2H), 7.50 (d, 2H).

Workup

  1. customThe catalyst was removed by filtration through diatomaceous earth
  2. washthe filter pad was washed with ethanol and ethyl acetate
  3. customThe volatiles were removed from the filtrate by evaporation
  4. customthe residue triturated with ether and hexane

Sources & evidence

ORD record
ord-ea10996620524120b6e6ff7aa80b2e1c
Source dataset
uspto-grants-2005_02
Patent number
US06855719B1

Reaction notes

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