3-Bromoaniline → 4-[(3-Bromophenyl)amino]-7-methoxy-3-quinolinecarbonitrile

HRID 1934893Notes

Reaction equation

HRID 1934893 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]#[N:15].[Br:16][C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][CH:23]=1)[NH2:20]>COC(O)C.CCOCC>[Br:16][C:17]1[CH:18]=[C:19]([NH:20][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=3)[N:5]=[CH:4][C:3]=2[C:14]#[N:15])[CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 115623-BromoanilineHCID 125594314-Chloro-7-methoxyquinoline-3-carbonitrile

Product 1

HCID 99504604-[(3-Bromophenyl)amino]-7-methoxy-3-quinolinecarbonitrileYield 33.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 30156371-MethoxyethanolSolvent

Procedure

A solution of 2.97 g (13.6 mmol) of 4-chloro-7-methoxy-3-quinolinecarbonitrile and 4.67 g (27.2 mmol) of 3-bromo aniline in 76 ml of methoxyethanol was refluxed under nitrogen for 5 hours. The solution was cooled and diluted with ether. Solid was collected and washed with ether. The solid was stirred with a hot mixture of ethyl acetate and sodium bicarbonate solution. The organic layer was separated and dried over magnesium sulfate. Solvent was removed and the residue was recrystallized from a chloroform-ethyl acetate mixture giving 1.6 g of 4-[(3-bromophenyl)amino]-7-methoxy-3-quinolinecarbonitrile as a white solid: mass spectrum (electrospray, m/e): M+H 354.1, 356.1.

Workup

  1. temperatureThe solution was cooled
  2. customSolid was collected
  3. washwashed with ether
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. customSolvent was removed
  7. customthe residue was recrystallized from a chloroform-ethyl acetate mixture

Sources & evidence

ORD record
ord-afc62d4ae0154a84a7f017847830048e
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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