Tert-Butyl nitrite → 5H-quinolino[8,7-c][1,2]benzothiazine 6,6-dioxide

HRID 513595Notes

Reaction equation

N[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[N:20]=[CH:19][CH:18]=[CH:17]2)(=[O:10])=[O:9].N(OC(C)(C)C)=O>C(O)(=O)C>[CH:17]1[C:16]2[C:21](=[C:12]3[C:13](=[CH:14][CH:15]=2)[C:4]2[C:3](=[CH:2][CH:7]=[CH:6][CH:5]=2)[S:8](=[O:10])(=[O:9])[NH:11]3)[N:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 10 °C

Procedure

2-Amino-N-(quinolin-8-yl)-benzenesulfonamide (Example Compound 8) (100 mg, 0.32 mmol) was dissolved in acetic acid (2 ml) and stirred at 10° C. for 5 min. The solution was cooled to −10° C. before tert-butyl nitrite (36 μl, 0.08 mmol) was added dropwise, the mixture was allowed to warm to room temperature and stirred for 10 minutes. The reaction was quenched with water and extracted with EtOAc. The organic phase was washed with a sat. sodium bicarbonate solution, brine, dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by column chromatography with MeOH/DCM/NH3 (1:100:2 drops) as the eluent to give the title compound (50 mg, 53%).

Workup

additionwas added dropwise
temperatureto warm to room temperature
stirringstirred for 10 minutes
customThe reaction was quenched with water
extractionextracted with EtOAc
washThe organic phase was washed with a sat. sodium bicarbonate solution, brine
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo
customThe crude residue was purified by column chromatography with MeOH/DCM/NH3 (1:100:2 drops) as the eluent

Sources & evidence

ORD record: ord-61c5a7d4b32d41a0a398ec1bff7d4eb4
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102688B2

Reaction notes

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