6-Nitro-2,3-dihydro-benzo[1,4]oxathiine-4,4-dioxide → 6-Amino-2,3-dihydro-1,4

HRID 1373719Notes

Reaction equation

HRID 1373719 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH2:11][CH2:10][S:9](=[O:14])(=[O:13])[C:8]=2[CH:15]=1)([O-])=O.[H][H]>C1COCC1.CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH2:11][CH2:10][S:9](=[O:14])(=[O:13])[C:8]=2[CH:15]=1

Participants

6

Reactant 2

HCID 219881646-Nitro-2,3-dihydro-benzo[1,4]oxathiine-4,4-dioxideHCID 178418361HCID 178418361, compound

Product 1

HCID 219881516-Amino-2,3-dihydro-1,4Yield 46.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.917 g 6-Nitro-2,3-dihydro-benzo[1,4]oxathiine-4,4-dioxide (from g)) were hydrogenated in a mixture of 20 ml THF and 20 ml MeOH with 0.90 g 5% Pd—C at atmospheric hydrogen pressure for 90 min. at room temperature. The catalyst was filtered off, the filtrate evaporated and the residue chromatographed on silica to yield 370 mg of the title compound.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate evaporated
  3. customthe residue chromatographed on silica

Sources & evidence

ORD record
ord-ef96b7afa3474a44a6945b1e95e04c89
Source dataset
uspto-grants-2007_01
Patent number
US07163941B2

Reaction notes

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