4-Methoxy-2-nitrobenzenesulphonyl chloride → 2-Nitro-4-methoxy-N-(2-methyl-quinolin-8-yl)-benzenesulfonamide

HRID 513507Notes

Reaction equation

HRID 513507 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([NH2:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[C:17]([N+:25]([O-:27])=[O:26])[CH:16]=1>CN(C1C=CN=CC=1)C>[N+:25]([C:17]1[CH:16]=[C:15]([O:14][CH3:13])[CH:20]=[CH:19][C:18]=1[S:21]([NH:12][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([CH3:1])[CH:11]=[CH:10]2)(=[O:23])=[O:22])([O-:27])=[O:26]

Participants

4

Reactant 2

HCID 874524-Methoxy-2-nitrobenzenesulphonyl chlorideHCID 1404572-Methyl-8-aminoquinoline2×

Product 1

HCID 236319492-Nitro-4-methoxy-N-(2-methyl-quinolin-8-yl)-benzenesulfonamideYield 51.8%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

In a similar fashion using route 14 general procedure 27, 2-methyl-quinolin-8-ylamine (Intermediate 22) (500 mg, 3.1 mmol) and 4-methoxy-2-nitrobenzenesulfonyl chloride (826 mg, 3.4 mmol) and DMAP (19 mg, 1.5 mmol) gave the title compound (600 mg, 51%).

Sources & evidence

ORD record
ord-64139ef3c8ba40929d663ea8f85cacbf
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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