4-Fluoroaniline → 4-[(4-Fluorophenyl)amino]-6,7-dimethoxyquinoline-3-carbonitrile

HRID 612011Notes

Reaction equation

HRID 612011 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].[F:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1.C(OC(O)C)C>N1C=CC=CC=1>[F:18][C:19]1[CH:25]=[CH:24][C:22]([NH:23][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:21][CH:20]=1

Participants

5

Reactant 3

HCID 97314-FluoroanilineHCID 101298981-EthoxyethanolHCID 105866764-Chloro-6,7-dimethoxy-quinoline-3-carbonitrile

Product 1

HCID 53288464-[(4-Fluorophenyl)amino]-6,7-dimethoxyquinoline-3-carbonitrileYield 90.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 0.5 g of 4-chloro-6,7-dimethoxy-3-quinolinecarbonitrile, 0.44 g of 4-fluoroaniline, 0.16 ml of pyridine, and 6 ml of ethoxyethanol was stirred, under nitrogen, at reflux temperature for 4 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 to give 0.59 g of 4-[(4-fluorophenyl)amino]-6,7-dimethoxy-3-quinolinecarbonitrile as a solid, mp 282-285° C.

Workup

  1. temperatureat reflux temperature for 4 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

Sources & evidence

ORD record
ord-dbc822e08482414897e5eb74ce5cf301
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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