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

HRID 513518Notes

Reaction equation

HRID 513518 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([NH2:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[N+:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[S:22](Cl)(=[O:24])=[O:23])([O-:15])=[O:14].N1C=CC=CC=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([NH:12][S:22]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[N+:13]([O-:15])=[O:14])(=[O:23])=[O:24])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 126042744-Chloroquinolin-8-amine2×

Product 1

HCID 68182953N-(4-Chloro-quinolin-8-yl)-2-nitro-benzenesulfonamideYield 75%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In a similar fashion using route 14 general procedure 27, 4-chloro-quinolin-8-ylamine (Intermediate 464) (1.5 g, 8.43 mmol), 2-nitrobenzene-1-sulfonyl chloride (2.43 g, 11.0 mmol), DMAP (cat), pyridine (2 ml, 25.28 mmol) in DCM (70 ml) for 3 h at room temperature gave the title compound (2.3 g, 74%) after purification by column chromatography with DCM as the eluent.

Workup

  1. customfor 3 h
  2. customat room temperature

Sources & evidence

ORD record
ord-a2ba242c68ec477dabda3015c389c6c9
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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