6-Methoxy-8-quinolinamine → N-(5-methoxyquinolin-8-yl)-2-nitrobenzenesulfonamide

HRID 513517Notes

Reaction equation

HRID 513517 reaction equation
COC1C=C2C(=C(N)C=1)N=CC=C2.[CH3:14][O:15][C:16]1[CH:25]=[CH:24][C:23]([NH2:26])=[C:22]2[C:17]=1[CH:18]=[CH:19][CH:20]=[N:21]2.[N+:27]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[S:36](Cl)(=[O:38])=[O:37])([O-:29])=[O:28]>>[CH3:14][O:15][C:16]1[CH:25]=[CH:24][C:23]([NH:26][S:36]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[N+:27]([O-:29])=[O:28])(=[O:37])=[O:38])=[C:22]2[C:17]=1[CH:18]=[CH:19][CH:20]=[N:21]2

Participants

4

Reactant 3

HCID 70236-Methoxy-8-quinolinamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 7771105-Methoxyquinolin-8-amine

Product 1

HCID 68183469N-(5-methoxyquinolin-8-yl)-2-nitrobenzenesulfonamideYield 64%

Procedure

In a similar fashion using route 14 general procedure 27, 6-methoxyquinolin-8-amine (Intermediate 67) (350 mg, 2.01 mmol) and 2-nitrobenzenesulfonyl chloride (533 mg, 2.41 mmol) gave the title compound (460 mg, 64%) after purification by column chromatography with DCM as the eluent.

Sources & evidence

ORD record
ord-baa967f0756c4a738e50b737b426a6ae
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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