Stannous chloride dihydrate → 2-Amino-N-(2-methyl-quinolin-8-yl)-benzenesulfonamide

HRID 513550Notes

Reaction equation

HRID 513550 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([NH:12][S:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N+:22]([O-])=O)(=[O:15])=[O:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.O.O.[Sn](Cl)Cl>>[NH2:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[S:13]([NH:12][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([CH3:1])[CH:11]=[CH:10]2)(=[O:15])=[O:14]

Participants

3

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 16759518N-(2-Methyl-quinolin-8-yl)-2-nitro-benzenesulfonamide2×

Product 1

HCID 167595192-Amino-N-(2-methyl-quinolin-8-yl)-benzenesulfonamideYield 47.2%

Procedure

In a similar fashion using route 15 general procedure 29, N-(2-methyl-quinolin-8-yl)-2-nitro-benzenesulfonamide (Intermediate 149) (423 mg, 1.23 mmol) and tin (II) chloride dihydrate (701 mg, 3.70 mmol) gave the title compound (182 mg, 47%) after purification by column chromatography with DCM/MeOH (99:1-95:5) gradient elution.

Sources & evidence

ORD record
ord-d6f5f4abbf844d54b5441aec58f8437d
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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