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

HRID 1452052노트

반응식

HRID 1452052 반응식
[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]

참가 물질

4

반응물 2

HCID 69803Diethyl acetylenedicarboxylateHCID 189298993-Bromo-5-ethylaniline

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-55aaead4d56e4311adf1be54e5afe732
출처 데이터셋
uspto-grants-1997_02
특허 번호
US05606063

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