O-Toluidine → HCID 19356228, compound

HRID 377620Notes

Reaction equation

HRID 377620 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:4](=[O:18])[C:3]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20].[NH2:24][C:25]1[C:26]([CH3:31])=[CH:27][CH:28]=[CH:29][CH:30]=1>C(Cl)(Cl)Cl>[CH3:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[NH:24][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:4](=[O:18])[C:3]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

4

Reactant 2

HCID 7242O-ToluidineHCID 2786148HCID 2786148, compound

Product 1

HCID 19356228HCID 19356228, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture consisting of 1.0 g (3.05 mmol) of ethyl 4-chloro-2-oxo-1-phenyl-1,2-dihydroquinoline-3-carboxylate and 6.5 g (60.7 mmol) of o-toluidine was reacted at 100° C. for 5 hours. After the reaction, chloroform was added, and the resultant mixture was washed with a 5% aqueous solution of potassium hydrogensulfate and was then dried. The solvent was distilled off under reduced pressure, and the residue so obtained was purified by chromatography on a silica gel and was then recrystallized from ethanol/water, whereby 0.844 g of ethyl 4-(2-methylphenylamino)-2-oxo-1-phenyl-1,2-dihydroquinoline-3-carboxylate (Compound No. 33) was obtained (yield: 69.5%).

Workup

  1. customwas reacted at 100° C. for 5 hours
  2. additionwas added
  3. washthe resultant mixture was washed with a 5% aqueous solution of potassium hydrogensulfate
  4. customwas then dried
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue so obtained
  7. customwas purified by chromatography on a silica gel
  8. customwas then recrystallized from ethanol/water

Sources & evidence

ORD record
ord-6639849fe1744e57a5616a6e4ecb3874
Source dataset
uspto-grants-2000_02
Patent number
US06028081

Reaction notes

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