Pyridine → 3-Nitro-pyridine-2-sulfonic acid quinolin-8-ylamide

HRID 513530

Reaction equation

HRID 513530 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[N+:12]([C:15]1[C:16]([S:21](Cl)(=[O:23])=[O:22])=[N:17][CH:18]=[CH:19][CH:20]=1)([O-:14])=[O:13].N1C=CC=CC=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[N:10]1[C:11]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[NH:1][S:21]([C:16]2[C:15]([N+:12]([O-:14])=[O:13])=[CH:20][CH:19]=[CH:18][N:17]=2)(=[O:23])=[O:22])[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 113598-AminoquinolineHCID 543288413-Nitropyridine-2-sulfonyl chloride

Product 1

HCID 681832803-Nitro-pyridine-2-sulfonic acid quinolin-8-ylamideYield 42%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In a similar fashion using route 14 general procedure 27, 8-aminoquinoline (1.3 g, 9.36 mmol), 3-nitro-pyridine-2-sulfonyl chloride 445 (2.7 g, 12.2 mmol), pyridine (2.25 ml, 28.1 mmol), DMAP (cat.) and DCM (100 ml) gave the title compound (1.3 g, 42%) after purification by column chromatography with DCM as the eluent.

Sources & evidence

ORD record
ord-051dbd3e7d654674b958a518d5ed6c11
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Linked notes

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