4-Bromoaniline → 4-[(4-Bromophenyl)amino]-6-nitro-3-quinolinecarbonitrile

HRID 379129Notes

Reaction equation

HRID 379129 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:15]#[N:16].[Br:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1>C(O)C>[Br:17][C:18]1[CH:24]=[CH:23][C:21]([NH:22][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:15]#[N:16])=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 78074-BromoanilineHCID 110856904-Chloro-6-nitroquinoline-3-carbonitrile

Product 1

HCID 224667624-[(4-Bromophenyl)amino]-6-nitro-3-quinolinecarbonitrileYield 44.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5.00 g (21.5 mmol) 4-chloro-6-nitro-quinoline-3-carbonitrile, 200 ml ethanol, and 4.42 g (25.8 mmol) p-bromoaniline was heated to reflux under N2 for 3 hours. Removed heat and added saturated sodium bicarbonate until basic. Stripped solvents and azeotroped with ethanol. Slurried residue with hexane, collected solids, and air dried. Washed with water and dried in vacuo. Boiled in 1.4 liters ethyl acetate, and without completely dissolving all solids, stirred with Darco, and filtered. Stripped solvent and dried in vacuo, giving 3.524 g of yellow solid: mass spectrum (electrospray m/e): M+H=369, 370.9.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under N2 for 3 hours
  3. customRemoved
  4. temperatureheat
  5. additionadded saturated sodium bicarbonate until basic
  6. customStripped solvents and azeotroped with ethanol
  7. customSlurried residue with hexane, collected solids, and air
  8. customdried
  9. washWashed with water
  10. customdried in vacuo
  11. dissolutionBoiled in 1.4 liters ethyl acetate, and without completely dissolving all solids
  12. filtrationfiltered
  13. customStripped solvent and dried in vacuo

Sources & evidence

ORD record
ord-6c37a267eb11494bbef5fb806d671b6d
Source dataset
uspto-grants-2001_10
Patent number
US06297258B1

Reaction notes

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