Stannous Chloride → 2-Amino-N-(5-benzyloxy-quinolin-8-yl)-benzenesulfonamide

HRID 513801Notes

Reaction equation

HRID 513801 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]([NH:19][S:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[N+:29]([O-])=O)(=[O:22])=[O:21])=[C:15]2[C:10]=1[CH:11]=[CH:12][CH:13]=[N:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[Sn]Cl>CCO>[NH2:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[S:20]([NH:19][C:16]1[CH:17]=[CH:18][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:10]2[C:15]=1[N:14]=[CH:13][CH:12]=[CH:11]2)(=[O:21])=[O:22]

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 68183366N-(5-Benzyloxy-quinolin-8-yl)-2-nitro-benzenesulfonamide

Product 1

HCID 681835052-Amino-N-(5-benzyloxy-quinolin-8-yl)-benzenesulfonamideYield 86.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a similar fashion using route 19 general procedure 29, N-(5-benzyloxy-quinolin-8-yl)-2-nitro-benzenesulfonamide 566 (519 mg, 1.19 mmol), SnCl2 (1.08 g, 4.77 mmol), and EtOH (10 ml) gave the title compound (417 mg, 86%) which was used in the next step without further purification.

Sources & evidence

ORD record
ord-d4c270105af146e7a60ef5af951b4aab
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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