Diethyl (ethoxymethylene)malonate → Ethyl 8-bromo-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 1005669Notes

Reaction equation

HRID 1005669 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].C([O:11][CH:12]=[C:13]([C:19](OCC)=O)[C:14]([O:16][CH2:17][CH3:18])=[O:15])C>>[C:14]([C:13]1[CH:19]=[N:4][C:3]2[C:5]([C:12]=1[OH:11])=[CH:6][CH:7]=[CH:8][C:2]=2[Br:1])([O:16][CH2:17][CH3:18])=[O:15]

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 119922-Bromoaniline

Product 1

HCID 178469454Ethyl 8-bromo-4-oxo-1,4-dihydroquinoline-3-carboxylateYield 58%

Conditions

Temperature
100 °C

Procedure

A mixture of 50 g (0.291 mol) of 2-bromoaniline and 63 g (0.291 mol) of diethyl ethoxymethylenemalonate was heated at 100° C. under a reduced pressure for 3 hours, followed by heating at 200° C. for further 12 hours. After the completion of the reaction, the solid matter in the resulting reaction mixture was washed with ethyl acetate, and the crystals were collected by filtration and dried, to give 50 g of the title compound.

Workup

  1. temperatureby heating at 200° C. for further 12 hours
  2. customAfter the completion of the reaction
  3. customthe solid matter in the resulting reaction mixture
  4. washwas washed with ethyl acetate
  5. filtrationthe crystals were collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-16d7dfd0bcbf421192ab35502bdcbaa4
Source dataset
uspto-grants-2004_09
Patent number
US06787534B2

Reaction notes

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