8-Aminoquinoline → 2-nitro-N-(quinolin-8-yl)benzenesulfonamide

HRID 513502Notes

Reaction equation

HRID 513502 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10](Cl)(=[O:12])=[O:11])([O-:3])=[O:2].[NH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:24]=1[N:23]=[CH:22][CH:21]=[CH:20]2>C(Cl)Cl>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:14][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:24]=1[N:23]=[CH:22][CH:21]=[CH:20]2)(=[O:12])=[O:11])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 113598-AminoquinolineHCID 155402-Nitrobenzenesulfonyl chloride

Product 1

HCID 7394492-nitro-N-(quinolin-8-yl)benzenesulfonamideYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Nitrobenzenesulfonyl chloride (1.15 g, 5.21 mmol) was added to a stirred solution of 8-aminoquinoline (500 mg, 3.47 mmol) and TEA (0.72 ml, 5.21 mmol) in DCM (5 ml), at 0° C., under argon. The reaction was allowed to warm to room temperature and was stirred for 5 h. The mixture was concentrated in vacuo. The residue was dissolved in EtOAc, washed with water and a sat. sodium bicarbonate solution. The organic phase was dried (Na2SO4) and concentrated in vacuo to give the title compound (980 mg, 86%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with water
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c71572f5c2fd416c8bfe5bab833c921f
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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