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

HRID 9719Notes

Reaction equation

HRID 9719 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-f629534e45f24ca1b3eebffb5d964052
Source dataset
uspto-grants-2006_08
Patent number
US07091345B2

Reaction notes

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