m-Toluidine → Ethyl 7-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 1168809Notes

Reaction equation

HRID 1168809 reaction equation
C(O[CH2:4][CH:5]([C:11]([O:13]CC)=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[CH:18]=1>C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>[OH:13][C:11]1[C:22]2[C:17](=[CH:18][C:19]([CH3:23])=[CH:20][CH:21]=2)[N:16]=[CH:4][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

4

Reactant 2

HCID 7934m-ToluidineHCID 98702Diethyl (ethoxymethyl)malonate

Product 1

HCID 178469524Ethyl 7-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylateYield 76.3%

Reagents, catalysts & solvents 1

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)Solvent

Conditions

Temperature
100 °C

Procedure

Diethyl ethoxymethylmalonate (37.8 mL, 187 mmol) and m-toluidine (20.0 mL, 187 mmol) were combined and heated at 100° C. for about 3 hours. The reaction mixture was allowed to cool to ambient temperature and it solidified. Dowtherm A (350 mL) was added and the reaction mixture was heated at reflux for about 30 minutes. The reaction mixture was allowed to cool to ambient temperature. The resulting precipitate was isolated by filtration, rinsed with acetone and dried to provide 33 g of ethyl 4-hydroxy-7-methyl-3-quinolinecarboxylate as a tan powder.

Workup

  1. temperatureto cool to ambient temperature
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux for about 30 minutes
  4. temperatureto cool to ambient temperature
  5. customThe resulting precipitate was isolated by filtration
  6. washrinsed with acetone
  7. customdried

Sources & evidence

ORD record
ord-72e9b4f0f2124d4897ce0f7282f196bf
Source dataset
uspto-grants-2003_09
Patent number
US06627640B2

Reaction notes

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