Diethyl acetylenedicarboxylate → Ethyl 7-bromo-5-ethyl-4-oxo-1,4-dihydroquinoline-2-carboxylate

HRID 1452052Notes

Reaction equation

HRID 1452052 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([CH2:9][CH3:10])[CH:8]=1)[NH2:5].[CH2:11]([O:13][C:14]([C:16]#[C:17][C:18](OCC)=[O:19])=[O:15])[CH3:12]>CO>[CH2:9]([C:7]1[CH:8]=[C:2]([Br:1])[CH:3]=[C:4]2[C:6]=1[C:18](=[O:19])[CH:17]=[C:16]([C:14]([O:13][CH2:11][CH3:12])=[O:15])[NH:5]2)[CH3:10]

Participants

4

Reactant 2

HCID 69803Diethyl acetylenedicarboxylateHCID 189298993-Bromo-5-ethylaniline

Product 1

HCID 19735211Ethyl 7-bromo-5-ethyl-4-oxo-1,4-dihydroquinoline-2-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve 3-bromo-5-ethylaniline (4.7g, 23.5mmol) in methanol (100mL) and add diethylacetylene dicarboxylate (5.5mL) at room temperature. Reflux for 10 hours and cool to room temperature. Evaporate the solvent in vacuo and add to diphenylether (100mL) at 250° C. Stir for 15 minutes and let cool to room temperature. Add hexane (500mL) and filter the precipitate. Purify by silica gel chromatography to give 5-ethyl-7-bromo-4-oxo-1,4-dihydroquinoline-2-carboxylic acid, ethyl ester

Workup

  1. temperatureReflux for 10 hours
  2. customEvaporate the solvent in vacuo
  3. additionadd to diphenylether (100mL) at 250° C
  4. temperaturelet cool to room temperature
  5. filtrationAdd hexane (500mL) and filter the precipitate
  6. customPurify by silica gel chromatography

Sources & evidence

ORD record
ord-55aaead4d56e4311adf1be54e5afe732
Source dataset
uspto-grants-1997_02
Patent number
US05606063

Reaction notes

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