Hydrochloric Acid → 2-Amino-N-(4-chloro-quinolin-8-yl)-benzenesulfonamide

HRID 513555Notes

Reaction equation

HRID 513555 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([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:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.Cl[Sn]Cl.Cl>CCO>[NH2:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[S:13]([NH:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[N:5]=[CH:4][CH:3]=[C:2]2[Cl:1])(=[O:15])=[O:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24479Stannous ChlorideHCID 68182953N-(4-Chloro-quinolin-8-yl)-2-nitro-benzenesulfonamide2×

Product 1

HCID 681834662-Amino-N-(4-chloro-quinolin-8-yl)-benzenesulfonamideYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a similar fashion using route 1 general procedure 4, N-(4-chloro-quinolin-8-yl)-2-nitro-benzenesulfonamide (Intermediate 246) (2.3 g, 6.32 mmol), SnCl2 (5.99 g, 31.6 mmol) and 6N HCl (cat.) in EtOH (30 ml) at 90° C. for 22 h gave the title compound (1.35 g, 64%) which was used in the next step without further purification.

Workup

  1. customat 90° C.
  2. customfor 22 h

Sources & evidence

ORD record
ord-fad2a4b76da94480b18e16d5dbd919f2
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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