Pyridine → 4-Chloro-N-(2-chloro-quinolin-8-yl)-2-nitro-benzenesulfonamide

HRID 513529Notes

Reaction equation

HRID 513529 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1.[Cl:15][C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[C:19]([NH2:26])[CH:20]=[CH:21][CH:22]=2)[N:17]=1.N1C=CC=CC=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:26][C:19]2[CH:20]=[CH:21][CH:22]=[C:23]3[C:18]=2[N:17]=[C:16]([Cl:15])[CH:25]=[CH:24]3)(=[O:10])=[O:9])=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 206314-Chloro-2-nitrophenylsulfonyl chloride2×HCID 3465192-Chloroquinolin-8-amine2×

Product 1

HCID 866697584-Chloro-N-(2-chloro-quinolin-8-yl)-2-nitro-benzenesulfonamideYield 23%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In a similar fashion using route 14 general procedure 27, 4-chloro-2-nitrobenzene-1-sulfonyl chloride (Intermediate 454) (0.86 g, 3.37 mmol), 2-chloro-quinolin-8-ylamine (Intermediate 26) (0.5 g, 2.80 mmol), DMAP (cat), pyridine (0.68 ml, 8.42 mmol) and DCM (10 ml) gave the title compound (0.25 g, 23%) after purification by column chromatography DCM/MeOH (99:1) as the eluent.

Sources & evidence

ORD record
ord-bd6cc266440b49bf954edfde8140fce7
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

Loading…