Ethanol → 1,2-Dihydro-7-methoxy-4-phenyl-2-oxo-3-quinoline carboxylic acid ethyl ester

HRID 3153Notes

Reaction equation

HRID 3153 reaction equation
[NH2:1][C:2]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.C([C:20](CC)([C:24]([O-:26])=[O:25])[C:21]([O-:23])=O)C.[CH2:29](O)[CH3:30]>>[CH2:29]([O:26][C:24]([C:20]1[C:21](=[O:23])[NH:1][C:2]2[C:3]([C:4]=1[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[CH:12][CH:13]=[C:14]([O:16][CH3:17])[CH:15]=2)=[O:25])[CH3:30]

Participants

4

Reactant 3

HCID 702EthanolHCID 254180(2-Amino-4-methoxyphenyl)(phenyl)methanoneHCID 69515632,2-Diethylpropanedioate

Product 1

HCID 540116141,2-Dihydro-7-methoxy-4-phenyl-2-oxo-3-quinoline carboxylic acid ethyl esterYield 90.2%

Conditions

Temperature
160 °C

Procedure

A mixture of 2-amino-4-methoxybenzophenone (20 g, 88 mmol), diethylmalonate (26.7 ml, 176 mmol), 1,8-diazabicyclo[5,2,0]-undeca-7-en (DBU) (0.66 ml, 4.4 mmol) was stirred with heat at 160° C. for 2 hours. The reaction mixture was cooled by air. To the cooled mixture was added ethanol (30 ml) to obtain a precipitated crystal by filtration. The crystal obtained was washed with ethanol to give 25.7 g (yield: 90.2%) of the title compound.

Workup

  1. temperatureThe reaction mixture was cooled by air
  2. customto obtain a precipitated crystal
  3. filtrationby filtration
  4. customThe crystal obtained
  5. washwas washed with ethanol

Sources & evidence

ORD record
ord-c39dc7ddfdaf41718ff28171b32b7253
Source dataset
uspto-grants-1998_03
Patent number
US05733918

Reaction notes

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