3-Chloroaniline → 4-[(3-Chlorophenyl)amino]-6-nitro-3-quinolinecarbonitrile

HRID 548426Notes

Reaction equation

HRID 548426 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].[Cl:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][CH:24]=1)[NH2:21]>C(O)C>[Cl:17][C:18]1[CH:19]=[C:20]([NH:21][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:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 79323-ChloroanilineHCID 110856904-Chloro-6-nitroquinoline-3-carbonitrile

Product 1

HCID 224666744-[(3-Chlorophenyl)amino]-6-nitro-3-quinolinecarbonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 10.0 g (42.9 mmol)) 4-chloro-6-nitro-quinoline-3-carbonitrile, 260 ml ethanol, and 5.40 ml 3-chloroaniline was heated to reflux under N2. Removed heat at 4 hours, cooled to 25° C. and added saturated sodium bicarbonate until the pH was basic. Stripped solvents and azeotroped with ethanol. Slurried residue with hexane, collected solid, and air dried. Washed solids with water and dried in vacuo. Dissolved in boiling ethyl acetate, stirred with Darco, and filtered. Stripped solvent and dried residue in vacuo, giving 6.5 g of yellow solid: mass spectrum (electrospray m/e): M+H=325.0, 327.0.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under N2
  3. customRemoved
  4. temperatureheat at 4 hours
  5. additionadded saturated sodium bicarbonate until the pH
  6. customStripped solvents and azeotroped with ethanol
  7. customcollected solid, and air
  8. customdried
  9. washWashed solids with water
  10. customdried in vacuo
  11. dissolutionDissolved
  12. filtrationfiltered

Sources & evidence

ORD record
ord-53dede82bb9e4c36a3147737ad99a09c
Source dataset
uspto-grants-2011_05
Patent number
USRE042376E1

Reaction notes

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