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

HRID 513804Notes

Reaction equation

HRID 513804 reaction equation
[Cl:1][C:2]1[C:11]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N+:22]([O-])=O)(=[O:15])=[O:14])=[C:10]2[C:5]([C:6]([O:25][CH3:26])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.Cl[Sn]Cl>CCO>[NH2:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[S:13]([NH:12][C:11]1[C:2]([Cl:1])=[CH:3][CH:4]=[C:5]2[C:10]=1[N:9]=[CH:8][CH:7]=[C:6]2[O:25][CH3:26])(=[O:14])=[O:15]

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 68183070N-(7-Chloro-4-methoxy-quinolin-8-yl)-2-nitro-benzenesulfonamide

Product 1

HCID 681830532-Amino-N-(7-chloro-4-methoxy-quinolin-8-yl)-benzenesulfonamideYield 92.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a similar fashion using route 19 general procedure 29, N-(7-chloro-4-methoxy-quinolin-8-yl)-2-nitro-benzenesulfonamide 569 (580 mg, 1.4 mmol), SnCl2 (1.66 g, 7.3 mmol) in EtOH (20 ml) gave the title compound (470 mg, 92%) which was used in the next step without further purification.

Sources & evidence

ORD record
ord-b4d58d1aecf6403b97da0de248fd20cd
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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