HCID 18957785, compound → 6-Amino-3,4-dihydro-2,2-dioxo-4-oxo-1H-2,3-benzothiazine

HRID 2379370Notes

Reaction equation

HRID 2379370 reaction equation
[O:1]=[S:2]1(=[O:16])[NH:7][C:6](=[O:8])[C:5]2[CH:9]=[C:10]([N+:13]([O-])=O)[CH:11]=[CH:12][C:4]=2[CH2:3]1>[Pd].CO>[NH2:13][C:10]1[CH:11]=[CH:12][C:4]2[CH2:3][S:2](=[O:16])(=[O:1])[NH:7][C:6](=[O:8])[C:5]=2[CH:9]=1

Participants

4

Reactant 1

HCID 18957785HCID 18957785, compound

Product 1

HCID 189577826-Amino-3,4-dihydro-2,2-dioxo-4-oxo-1H-2,3-benzothiazineYield 102.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3,4-dihydro-2,2-dioxo-6-nitro-4-oxo-1H-2,3-benzothiazine (267 mg, 1.1 mmol) and 10% palladium on carbon (26 mg, 10% (w/w)) in methanol (50 ml) was hydrogenated at 50 psi for 30 min. The mixture was then filtered, the solid washed with methanol and the filtrates evaporated in vacuo to give the title compound (239 mg, 100%) as a yellow solid. 1H NMR (360 MHz, D6-DMSO) δ 3.87 (2H, s), 5.11 (2H, brs), 6.59 (1H, dd, J=8.0 and 2.5 Hz), 6.88 (1H, d, J=8.0 Hz), 7.15 (1H, d, J=2.5 Hz). MS (FAB) 211 (M-1).

Workup

  1. filtrationThe mixture was then filtered
  2. washthe solid washed with methanol
  3. customthe filtrates evaporated in vacuo

Sources & evidence

ORD record
ord-8254a5c208ae43858fcd8f0195485941
Source dataset
uspto-grants-1994_11
Patent number
US05360802

Reaction notes

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