Sodium Bicarbonate → 8-bromo-4-hydroxy-5-methoxy-3-Quinolinecarboxylic acid ethyl ester

HRID 423717ノート

反応式

HRID 423717 の反応式
C(O[C:4](=[O:22])[C:5](=[CH:11][NH:12][C:13]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=1[Br:21])[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.C(=O)(O)[O-].[Na+]>C(O)C>[CH2:9]([O:8][C:6]([C:5]1[C:4](=[O:22])[C:18]2[C:13](=[C:14]([Br:21])[CH:15]=[CH:16][C:17]=2[O:19][CH3:20])[NH:12][CH:11]=1)=[O:7])[CH3:10]

参加物

4

反応物 2

HCID 516892Sodium BicarbonateHCID 103846312-[(2-Bromo-5-methoxyphenylamino)methylene]malonic acid diethyl ester

生成物 1

HCID 102458028-bromo-4-hydroxy-5-methoxy-3-Quinolinecarboxylic acid ethyl ester収率 30%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

2-[(2-Bromo-5-methoxy-phenylamino)-methylene]-malonic acid diethyl ester (9 g, 24.2 mmol) was slowly added to polyphosphoric acid (30 g) at 120° C. The mixture was stirred at this temperature for additional 30 min and then cooled to room temperature. Absolute ethanol (30 mL) was added and the resulting mixture was refluxed for 30 min. The mixture was basified with aqueous sodium bicarbonate at 25° C. and extracted with EtOAc (4×100 mL). The organic layers were combined, dried and the solvent evaporated to give 8-bromo-5-methoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester (2.3 g, 30%).

後処理

  1. temperaturethe resulting mixture was refluxed for 30 min
  2. extractionextracted with EtOAc (4×100 mL)
  3. customdried
  4. customthe solvent evaporated

出典と根拠

ORDレコード
ord-cb871638aac243008881fd60b6683e13
出典データセット
uspto-grants-2012_01
特許番号
US08101767B2

反応ノート

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