Benzenesulfonyl chloride → N-5-Methylquinolin-8-yl-benzenesulfonamide

HRID 513471Notes

Reaction equation

HRID 513471 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]([NH2:12])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[C:13]1([S:19](Cl)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(Cl)Cl>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]([NH:12][S:19]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:21])=[O:20])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 128466255-Methylquinolin-8-amine2×

Product 1

HCID 68182878N-5-Methylquinolin-8-yl-benzenesulfonamideYield 28.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a similar fashion using route 14 general procedure 27, 5-methylquinolin-8-amine (Intermediate 44) (150 mg, 0.95 mmol) and benzenesulfonyl chloride (200 mg, 1.14 mmol) gave the title compound (80 mg, 28%) after column chromatography with DCM as the eluent.

Sources & evidence

ORD record
ord-9ebed34b7eba4396b37f1b42dfca45db
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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