Hydrochloric Acid → 2-Amino-4-chloro-N-(5-cyano-quinolin-8-yl)-benzenesulfonamide

HRID 513566Notes

Reaction equation

HRID 513566 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([C:22]#[N:23])=[C:16]3[C:21]=2[N:20]=[CH:19][CH:18]=[CH:17]3)(=[O:10])=[O:9])=[C:4]([N+:24]([O-])=O)[CH:3]=1.Cl[Sn]Cl.Cl>CCO>[NH2:24][C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]=1[S:8]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([C:22]#[N:23])=[C:16]2[C:21]=1[N:20]=[CH:19][CH:18]=[CH:17]2)(=[O:9])=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24479Stannous ChlorideHCID 681834404-Chloro-N-(5-cyano-quinolin-8-yl)-2-nitro-benzenesulfonamide2×

Product 1

HCID 681832792-Amino-4-chloro-N-(5-cyano-quinolin-8-yl)-benzenesulfonamideYield 139.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a similar fashion using route 1 general procedure 4, 4-chloro-N-(5-cyano-quinolin-8-yl)-2-nitro-benzenesulfonamide (Intermediate 273) (90 mg, 0.2 mmol), SnCl2 (28 mg, 1.3 mmol), 6N HCl (cat) and EtOH (6 ml) at 85° C. for 3 h gave the title compound (100 mg) which was used in the next step without further purification.

Workup

  1. customat 85° C.
  2. customfor 3 h

Sources & evidence

ORD record
ord-8f0ff6b40da04a69803557faf3c2deb3
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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