HCID 18957785, compound → 6-Amino-3,4-dihydro-2,2-dioxo-4-oxo-1H-2,3-benzothiazine
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]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
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).