Dimethylamine → 4-Dimethylamino-2-nitro-N-quinolin-8-yl-benzenesulfonamide

HRID 513760Notes

Reaction equation

HRID 513760 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:21]=2[N:20]=[CH:19][CH:18]=[CH:17]3)(=[O:10])=[O:9])=[C:4]([N+:22]([O-:24])=[O:23])[CH:3]=1.[CH3:25][NH:26][CH3:27]>O>[CH3:25][N:26]([CH3:27])[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:21]=2[N:20]=[CH:19][CH:18]=[CH:17]3)(=[O:10])=[O:9])=[C:4]([N+:22]([O-:24])=[O:23])[CH:3]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 167599244-Fluoro-2-nitro-N-quinolin-8-yl-benzenesulfonamide

Product 1

HCID 681833904-Dimethylamino-2-nitro-N-quinolin-8-yl-benzenesulfonamideYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

4-Fluoro-2-nitro-N-quinolin-8-yl-benzenesulfonamide 145 (0.13 g, 0.36 mmol) was dissolved in dimethyl amine (2M in THF; 1.77 ml, 3.59 mmol) and the mixture was heated at 90° C. in a sealed tube for 5 h. After cooling, water was added and the mixture was extracted with EtOAc. The organic phase was dried (Na2SO4) and concentrated in vacuo to give the title compound (0.13 g, 97%) which was used in the next step without further purification.

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with EtOAc
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-46812e160dd3498f8ebcb1bfe2d53345
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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