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

HRID 1421491Notes

Reaction equation

HRID 1421491 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].C([O:12][C:13]([C:15]1[C:16](=[O:29])[N:17]([CH3:28])[C:18]2[C:23]([C:24]=1[OH:25])=[C:22]([O:26][CH3:27])[CH:21]=[CH:20][CH:19]=2)=O)C.C(O)C>C1(C)C=CC=CC=1>[CH2:1]([N:3]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:13]([C:15]1[C:16](=[O:29])[N:17]([CH3:28])[C:18]2[C:23]([C:24]=1[OH:25])=[C:22]([O:26][CH3:27])[CH:21]=[CH:20][CH:19]=2)=[O:12])[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 7670N-EthylanilineHCID 54728881Ethyl 4-hydroxy-5-methoxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate

Product 1

HCID 54684693N-Ethyl-N-phenyl-1,2-dihydro-4-hydroxy-5-methoxy-1-methyl-2-oxo-quinoline-3-carboxamideYield 80%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-Ethylaniline (3.0 g, 25 mmol) was dissolved in 80 ml of toluene and about 30 ml of the solvent was distilled off in order to obtain a dry solution. To this boiling solution was added 1,2-dihydro-4hydroxy-5-methoxy-1-methyl-2-oxo-quinoline-3-carboxylic acid ethyl ester (2.7 g, 10 mmol). The ethanol formed during the reaction was distilled off together with some toluene for about 4 hours. The reaction 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 80%.

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-797c5f0fba5245e9aa5e1d6de75b1861
Source dataset
uspto-grants-2000_06
Patent number
US06077851

Reaction notes

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