Aniline → Ethyl 4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 227023

Reaction equation

HRID 227023 reaction equation
C(O[C:4](=[O:15])[C:5](=[CH:11]OCC)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH2:9]([O:8][C:6]([C:5]1[C:4](=[O:15])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH:11]=1)=[O:7])[CH3:10]

Participants

4

Reactant 2

HCID 6115AnilineHCID 6871Diethyl (ethoxymethylene)malonate

Product 1

HCID 220876Ethyl 4-oxo-1,4-dihydroquinoline-3-carboxylateYield 74.2%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Conditions

Temperature
260 °C

Procedure

31.7 g (147 mmol) of 2-Ethoxymethylene-malonic acid diethyl ester and 13.7 g (147 mmol) of aniline were stirred neat at 110° C. for 1 h, then 300 mL of diphenyl ether was added and the temperature of the oil bath was raised to 260° C. for 2 h. The solution was then cooled down to rt, diluted with 600 mL of hexanes and filtered. The solids were washed with 200 mL of hexanes and dried to yield 23.7 g of the product as a light brown powder. LC-MSD, m/z for C12H11NO3 [M+H]+=218.2, HPLC retention time: 2.5 min.

Workup

  1. temperatureThe solution was then cooled down to rt
  2. filtrationfiltered
  3. washThe solids were washed with 200 mL of hexanes
  4. customdried

Sources & evidence

ORD record
ord-ff3561eb1b8246a19701c5c21e4103cc
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Linked notes

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