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

HRID 1452052ノート

反応式

HRID 1452052 の反応式
[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]

参加物

4

反応物 2

HCID 69803Diethyl acetylenedicarboxylateHCID 189298993-Bromo-5-ethylaniline

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-55aaead4d56e4311adf1be54e5afe732
出典データセット
uspto-grants-1997_02
特許番号
US05606063

反応ノート

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