Ethanol → N-Methyl-N-phenyl-1,2-dihydro-4-hydroxy-5-methoxy-1-methyl-2-oxo-quinoline-3-carboxamide

HRID 395293Notes

Reaction equation

HRID 395293 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([O:11][C:12]([C:14]1[C:15](=[O:28])[N:16]([CH3:27])[C:17]2[C:22]([C:23]=1[OH:24])=[C:21]([O:25][CH3:26])[CH:20]=[CH:19][CH:18]=2)=O)C.C(O)C>C1(C)C=CC=CC=1>[CH3:1][N:2]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[C:12]([C:14]1[C:15](=[O:28])[N:16]([CH3:27])[C:17]2[C:22]([C:23]=1[OH:24])=[C:21]([O:25][CH3:26])[CH:20]=[CH:19][CH:18]=2)=[O:11]

Participants

5

Reactant 3

HCID 702EthanolHCID 7515N-MethylanilineHCID 54728881Ethyl 4-hydroxy-5-methoxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate

Product 1

HCID 54691517N-Methyl-N-phenyl-1,2-dihydro-4-hydroxy-5-methoxy-1-methyl-2-oxo-quinoline-3-carboxamideYield 83%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-Methylaniline (2.7g, 0.025 mol) was dissolved in 80 ml of toluene and about 30 ml of the solvent was distilled off in order to obtain a dry solution. 1,2-Dihydro-4-hydroxy-5-methoxy-1-methyl-2-oxo-quinoline-3-carboxylic acid ethyl ester (2.7 g, 0.01 mol) was added to the boiling solution. The ethanol formed during the reaction was distilled off together with some toluene for about 4 hours. The mixture was cooled to room temperature. The precipitate was collected, washed with cold toluene and hexane and dried to give the title compound (2.8 g), yield 83%.

Workup

  1. distillationabout 30 ml of the solvent was distilled off in order
  2. customto obtain a dry solution
  3. distillationwas distilled off together with some toluene for about 4 hours
  4. customThe precipitate was collected
  5. washwashed with cold toluene and hexane
  6. customdried

Sources & evidence

ORD record
ord-ed032e3b44ce4514a8fff1ca6d28f5c3
Source dataset
uspto-grants-2003_08
Patent number
US06605616B1

Reaction notes

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