Dimethyl Sulfoxide → 4-[(3-Bromophenyl)amino]-6,7-diethoxyquinoline-3-carbonitrile

HRID 1934931Notes

Reaction equation

HRID 1934931 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15](O)=[C:16]([OH:19])[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:21]#[N:22])[CH:5]=[CH:6][CH:7]=1.[CH2:23](I)[CH3:24].[C:26](=[O:29])([O-])[O-].[K+].[K+].[CH3:32]S(C)=O>>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:29][CH2:26][CH3:32])=[C:16]([O:19][CH2:23][CH3:24])[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:21]#[N:22])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 1354028484-(3-Bromophenylamino)-6,7-dihydroxy-3-quinolinecarbonitrile

Product 1

HCID 53288384-[(3-Bromophenyl)amino]-6,7-diethoxyquinoline-3-carbonitrile

Procedure

A mixture of 0.36 g of 4-[(3-bromophenyl)amino]-6,7-dihydroxy-3-quinolinecarbonitrile, 0.32 ml of ethyl iodide and 0.55 g of potassium carbonate in 4 ml of dimethylsulfoxide was stirred for 3 hours in an oil bath with heating. Most of the solvent was removed at reduced pressure. The mixture was mixed with ethyl acetate and water. The organic layer was washed with water and dried over magnesium sulfate. Solvent was removed to give 0.23 g of 4-[(3-bromophenyl)amino]-6,7-diethoxy-3-quinolinecarbonitrile which after recrystallization from ethyl acetate gave mp=173-175° C.

Workup

  1. temperaturewith heating
  2. customMost of the solvent was removed at reduced pressure
  3. additionThe mixture was mixed with ethyl acetate and water
  4. washThe organic layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customSolvent was removed

Sources & evidence

ORD record
ord-a76f2f701fd34c1992c11ad1c944c373
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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