Pyridine → N-(5-Methoxy-quinolin-8-yl)-2-nitro-4-trifluoromethyl-benzenesulfonamide

HRID 513819Notes

Reaction equation

HRID 513819 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([NH2:13])=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[N:8]2.[N+:14]([C:17]1[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][C:18]=1[S:27](Cl)(=[O:29])=[O:28])([O-:16])=[O:15].N1C=CC=CC=1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([NH:13][S:27]([C:18]2[CH:19]=[CH:20][C:21]([C:23]([F:25])([F:26])[F:24])=[CH:22][C:17]=2[N+:14]([O-:16])=[O:15])(=[O:28])=[O:29])=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[N:8]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 7771105-Methoxyquinolin-8-amineHCID 27757802-Nitro-4-(trifluoromethyl)benzene-1-sulfonyl chloride

Product 1

HCID 68183320N-(5-Methoxy-quinolin-8-yl)-2-nitro-4-trifluoromethyl-benzenesulfonamideYield 73.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a similar fashion using route 18 general procedure 27, 5-methoxy-quinolin-8-ylamine 586 (280 mg, 1.6 mmol), 2-nitro-4-(trifluoromethyl) benzenesulfonyl chloride (600 mg, 2.0 mmol), pyridine (0.39 ml, 4.8 mmol) DMAP (cat.) and DCM (15 ml) gave the title compound (500 mg, 73%) after purification by column chromatography with DCM as the eluent.

Sources & evidence

ORD record
ord-fb735ac125fa4316afcb78ba973106a8
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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