m-Toluidine → 6-Nitro-4-[(3-methylphenyl)amino]-3-quinolinecarbonitrile

HRID 548424Notes

Reaction equation

HRID 548424 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].[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[CH:19]=1.C(=O)(O)[O-].[Na+]>C(O)C>[N+:12]([C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][C:3]([C:15]#[N:16])=[C:2]2[NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[CH:19]=1)([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 7934m-ToluidineHCID 516892Sodium BicarbonateHCID 110856904-Chloro-6-nitroquinoline-3-carbonitrile

Product 1

HCID 224665426-Nitro-4-[(3-methylphenyl)amino]-3-quinolinecarbonitrileYield 73.7%

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 2.75 ml (25.7 mmol) 3-toluidine was heated to reflux for 4½ hours. Cooled and added a saturated sodium bicarbonate until pH was basic. Stripped solvents and azeotroped with ethanol. Slurried with hexane, collected, and air dried. Washed with water and dried in vacuo. Boiled in ethyl acetate, stirred with Darco and filtered. Stripped solvent and dried in vacuo to give 4.82 g of yellow-orange solid: mass spectrum (electrospray m/e): M+H=305.2.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4½ hours
  3. temperatureCooled
  4. customStripped solvents and azeotroped with ethanol
  5. customSlurried with hexane, collected
  6. customair dried
  7. washWashed with water
  8. customdried in vacuo
  9. filtrationfiltered
  10. customStripped solvent and dried in vacuo

Sources & evidence

ORD record
ord-9f4e185449f44f92a8ed44e014b1c763
Source dataset
uspto-grants-2011_05
Patent number
USRE042376E1

Reaction notes

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