2-Nitro-4-(trifluoromethyl)benzene-1-sulfonyl chloride → N-(7-Chloro-4-methoxy-quinolin-8-yl)-2-nitro-4-trifluoromethyl-benzenesulfonamide

HRID 513634Notes

Reaction equation

HRID 513634 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:5]=1[S:14](Cl)(=[O:16])=[O:15])([O-:3])=[O:2].[Cl:18][C:19]1[C:28]([NH2:29])=[C:27]2[C:22]([C:23]([O:30][CH3:31])=[CH:24][CH:25]=[N:26]2)=[CH:21][CH:20]=1>N1C=CC=CC=1>[Cl:18][C:19]1[C:28]([NH:29][S:14]([C:5]2[CH:6]=[CH:7][C:8]([C:10]([F:13])([F:12])[F:11])=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])(=[O:16])=[O:15])=[C:27]2[C:22]([C:23]([O:30][CH3:31])=[CH:24][CH:25]=[N:26]2)=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 27757802-Nitro-4-(trifluoromethyl)benzene-1-sulfonyl chlorideHCID 681832377-Chloro-4-methoxyquinolin-8-amine2×

Product 1

HCID 68183291N-(7-Chloro-4-methoxy-quinolin-8-yl)-2-nitro-4-trifluoromethyl-benzenesulfonamideYield 69.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Nitro-4-(trifluoromethyl)benzenesulfonyl chloride (839 mg, 2.9 mmol) was added to a solution of 7-chloro-4-methoxy-quinolin-8-ylamine (Intermediate 70) (550 mg, 2.6 mmol) in pyridine(10 ml) and the mixture was stirred at room temperature for 18 h. The solvent was removed in vacuo. The residue was dissolved EtOAc (100 ml), washed sat. sodium bicarbonate solution, dried (MgSO4) and concentrated in vacuo to give the title compound (830 mg, 69%).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved EtOAc (100 ml)
  3. washwashed sat. sodium bicarbonate solution
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a875d197522e45378a7150f949635fb6
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

Loading…