Hydrochloric Acid → 2-Amino-4-methyl-N-quinolin-8-yl-benzenesulfonamide

HRID 513553Notes

Reaction equation

HRID 513553 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:21]=2[N:20]=[CH:19][CH:18]=[CH:17]3)(=[O:10])=[O:9])=[C:4]([N+:22]([O-])=O)[CH:3]=1.[Sn](Cl)Cl.Cl>>[NH2:22][C:4]1[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][C:5]=1[S:8]([NH:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[N:20]=[CH:19][CH:18]=[CH:17]2)(=[O:10])=[O:9]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 24479Stannous ChlorideHCID 9735044-methyl-2-nitro-N-quinolin-8-ylbenzenesulfonamide2×

Product 1

HCID 167599222-Amino-4-methyl-N-quinolin-8-yl-benzenesulfonamideYield 17.2%

Procedure

In the similar fashion using route 1 general procedure 4, 4-methyl-2-nitro-N-quinolin-8-yl-benzenesulfonamide (Intermediate 151) (3.2 g, 9.3 mmol), tin (II) chloride (5.3 g, 2.79 mmol) and 6N HCl (2 ml) gave the title compound (500 mg, 17%).

Sources & evidence

ORD record
ord-5a2d012f7a3545edb968e522faa331dc
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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