Stannous Chloride → 2-Amino-N-(7-chloro-4-methoxy-quinolin-8-yl)-4-trifluoromethyl-benzenesulfonamide

HRID 513635Notes

Reaction equation

[Sn](Cl)Cl.[Cl:4][C:5]1[C:14]([NH:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][C:20]=2[N+:29]([O-])=O)(=[O:18])=[O:17])=[C:13]2[C:8]([C:9]([O:32][CH3:33])=[CH:10][CH:11]=[N:12]2)=[CH:7][CH:6]=1>CCO>[NH2:29][C:20]1[CH:21]=[C:22]([C:25]([F:27])([F:28])[F:26])[CH:23]=[CH:24][C:19]=1[S:16]([NH:15][C:14]1[C:5]([Cl:4])=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[C:9]2[O:32][CH3:33])(=[O:17])=[O:18]

Participants

Conditions

Temperature: 95 °C

Procedure

Tin (II) chloride (2.0 g, 9.0 mmol) was added to a solution of N-(7-chloro-4-methoxy-quinolin-8-yl)-2-nitro-4-trifluoromethyl-benzenesulfonamide (Intermediate 194) (830 mg, 1.8 mmol)) in EtOH (20 ml) and the mixture was heated at 95° C. for 2 h. After cooling the solvent was removed in vacuo. EtOAc (100 ml) was added and the solution cooled in an ice bath whilst aqueous NH3 was added until the solution was basic, the white precipitate formed was filtered and washed with EtOAc (100 ml). The combined organics were washed with brine (100 ml), dried (MgSO4) and concentrated in vacuo to give the title compound (670 mg, 86%).

Workup

temperatureAfter cooling the solvent
customwas removed in vacuo
additionEtOAc (100 ml) was added
temperaturethe solution cooled in an ice bath whilst aqueous NH3
additionwas added until the solution
customthe white precipitate formed
filtrationwas filtered
washwashed with EtOAc (100 ml)
washThe combined organics were washed with brine (100 ml)
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-9c98ac91610c4819913a9f84df63594f
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102688B2

Reaction notes

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