3-(Trifluoromethyl)aniline → HCID 5328842, compound

HRID 612007Notes

Reaction equation

HRID 612007 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]([F:28])([F:27])[C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][CH:26]=1)[NH2:23].C(OC(O)C)C>N1C=CC=CC=1>[F:18][C:19]([F:27])([F:28])[C:20]1[CH:21]=[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:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 73753-(Trifluoromethyl)anilineHCID 101298981-EthoxyethanolHCID 105866764-Chloro-6,7-dimethoxy-quinoline-3-carbonitrile

Product 1

HCID 5328842HCID 5328842, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 1.24 g of 4-chloro-6,7-dimethoxy-3-quinolinecarbonitrile, 1.61 g of 3-trifluoromethylaniline, 0.4 ml of pyridine, and 15 ml of ethoxyethanol was stirred, under nitrogen, at reflux temperature for 5 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 1.34 g of 4-[(3-trifluoromethylphenyl)amino]-6,7-dimethoxy-3-quinolinecarbonitrile as a solid, mp 190-193° C.

Workup

  1. temperatureat reflux temperature for 5 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-07d7226719b6499da108b3fb9ad82cff
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

Loading…