3-Aminobenzonitrile → HCID 5328845, compound

HRID 1934929Notes

Reaction equation

HRID 1934929 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].[NH2:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[C:22]#[N:23].C(OC(O)C)C>N1C=CC=CC=1>[C:22]([C:21]1[CH:20]=[C:19]([NH:18][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:26]=[CH:25][CH:24]=1)#[N:23]

Participants

5

Reactant 3

HCID 167023-AminobenzonitrileHCID 101298981-EthoxyethanolHCID 105866764-Chloro-6,7-dimethoxy-quinoline-3-carbonitrile

Product 1

HCID 5328845HCID 5328845, compoundYield 88.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 0.5 g of 4-chloro-6,7-dimethoxy-3-quinolinecarbonitrile, 0.47 g of 3-aminobenzonitrile, 0.16 ml of pyridine, and 12 ml of ethoxyethanol was stirred, under nitrogen, at reflux temperature for 22 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 0.59 g of 4-[(3-cyanophenyl)amino]-6,7-dimethoxy-3-quinolinecarbonitrile as a solid, mp 285-288° C.

Workup

  1. temperatureat reflux temperature for 22 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-7830f8288cee444ca32ac73899ba8e8c
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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