Sulfuric Acid → HCID 86670035, compound

HRID 1405277Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([N:18]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH2:21][CH2:20][CH2:19]3)=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:28]([O:30][CH3:31])=[O:29])[CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.[S:32](=[O:36])(=O)(O)[OH:33].S(Cl)([Cl:39])=O.C(OCC)(=O)C>C(Cl)(Cl)Cl>[Cl:39][S:32]([C:24]1[CH:23]=[C:22]2[C:27](=[CH:26][CH:25]=1)[N:18]([C:17]1[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[N:9][C:10]3[C:15]([N:16]=1)=[CH:14][C:13]([C:28]([O:30][CH3:31])=[O:29])=[CH:12][CH:11]=3)[CH2:19][CH2:20][CH2:21]2)(=[O:36])=[O:33]

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of methyl 2-(4-fluorophenyl)-3-(1,2,3,4-tetrahydroquinolin-1-yl)quinoxaline-6-carboxylate (300 mg, 0.73 mmol) in chloroform (50 mL) was added sulfuric acid (213.6 mg, 2.18 mmol) and thionyl chloride (514 mg, 4.36 mmol) dropwise with stirring at 85° C. for 3 h in an oil bath. The reaction was then quenched by the addition of ice-water, extracted with dichloromethane (3×80 mL). The organic layers combined and dried over magnesium sulfate, concentrated under vacuum to give the residue, which was applied onto a silica gel column with 2% ethyl acetate in petroleum to afford methyl 3-[6-(chlorosulfonyl)-1,2,3,4-tetrahydroquinolin-1-yl]-2-(4-fluorophenyl)quinoxaline-6-carboxylate as a yellow solid (260 mg, 70%).

Workup

customThe reaction was then quenched by the addition of ice-water
extractionextracted with dichloromethane (3×80 mL)
dry with materialdried over magnesium sulfate
concentrationconcentrated under vacuum
customto give the residue, which

Sources & evidence

ORD record: ord-14c878fb40cc430f868c5f5270fa20bb
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916561B2

Reaction notes

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