3-Chloroaniline → 4-[(3-Chlorophenyl)amino]-6,7-dimethoxyquinoline-3-carbonitrile

HRID 1934925Notes

Reaction equation

HRID 1934925 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]#[N:17].[Cl:18][C:19]1[CH:20]=[C:21]([CH:23]=[CH:24][CH:25]=1)[NH2:22].C(OC(O)C)C>N1C=CC=CC=1>[Cl:18][C:19]1[CH:20]=[C:21]([NH:22][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:16]#[N:17])[CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 79323-ChloroanilineHCID 101298981-EthoxyethanolHCID 105866764-Chloro-6,7-dimethoxy-quinoline-3-carbonitrile

Product 1

HCID 53288414-[(3-Chlorophenyl)amino]-6,7-dimethoxyquinoline-3-carbonitrileYield 54.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 0.5 g of 4-chloro-6,7-dimethoxy-3-quinolinecarbonitrile, 0.51 g of 3-chloroaniline, 0.16 ml of pyridine, and 6 ml of ethoxyethanol was stirred under nitrogen, at reflux temperature for 6 h. The mixture was cooled and partitioned with dichloromethane and aqueous sodium bicarbonate. The organic layer was washed with water, dried and evaporated. The residue was recrystallized from ethyl acetate-hexanes to give 0.37 g of 4-[(3-chlorophenyl)amino]-6,7-dimethoxy-3-quinolinecarbonitrile as a solid, mp 214-217° C.

Workup

  1. temperatureat reflux temperature for 6 h
  2. temperatureThe mixture was cooled
  3. custompartitioned with dichloromethane and aqueous sodium bicarbonate
  4. washThe organic layer was washed with water
  5. customdried
  6. customevaporated
  7. customThe residue was recrystallized from ethyl acetate-hexanes

Sources & evidence

ORD record
ord-ad3267a056a049898c1d0b40902e8dab
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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