Methylamine → N-(4-Methylamino-quinolin-8-yl)-benzenesulfonamide

HRID 513756Notes

Reaction equation

HRID 513756 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([NH:12][S:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[CH3:22][NH2:23]>>[CH3:22][NH:23][C:2]1[C:11]2[C:6](=[C:7]([NH:12][S:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 68183402N-(4-Chloro-quinolin-8-yl)-benzenesulfonamide

Product 1

HCID 68183247N-(4-Methylamino-quinolin-8-yl)-benzenesulfonamideYield 13%

Procedure

In a similar fashion using route 48 general procedure 114, N-(4-chloro-quinolin-8-yl)-benzenesulfonamide 224 (80 mg, 0.25 mmol), methyl amine (2M in THF; 1.23 ml, 2.50 mmol) at 100° C. for 48 h gave the title compound (10 mg, 13%) after purification by column chromatography with chloroform/MeOH (1 drop NH3) (98:2) as the eluent followed by recrystallisation from MeOH/DCM.

Workup

  1. customat 100° C.
  2. customfor 48 h

Sources & evidence

ORD record
ord-38c6dd4813be4d3c9208f3c5752d5209
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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