Diethyl Malonate → Ethyl 6-chloro-2-oxo-4-phenyl-1,2-dihydro-3-quinolinecarboxylate

HRID 1497053

반응식

HRID 1497053 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=O.[CH2:17]([O:19][C:20](=[O:27])[CH2:21][C:22](OCC)=[O:23])[CH3:18].C1CCN2C(=NCCC2)CC1>>[CH2:17]([O:19][C:20]([C:21]1[C:22](=[O:23])[NH:1][C:2]2[C:3]([C:9]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[CH:4][C:5]([Cl:8])=[CH:6][CH:7]=2)=[O:27])[CH3:18]

참가 물질

4

반응물 3

HCID 7761Diethyl MalonateHCID 128702-Amino-5-chlorobenzophenoneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

생성물 1

HCID 738703Ethyl 6-chloro-2-oxo-4-phenyl-1,2-dihydro-3-quinolinecarboxylate수율 49.5%

반응 조건

온도
185 °C

실험 절차

To a mixture of (2-amino-5-chloro-phenyl)-phenyl-methanone (5 g, 21.58 mmol) and malonic acid diethyl ester (4.565 ml, 30.21 mmol) was added DBU (0.45 ml, 3.02 mmol) under nitrogen and the mixture was stirred at 180-190° C. for 16 h. After cooling, the crude residue was purified by flash column chromatography (100-200 mesh silica, eluting with 50% ethyl acetate in hexane) to afford pure 6-chloro-2-oxo-4-phenyl-1,2-dihydro-quinoline-3-carboxylic acid ethyl ester (3.5 g, 49%) as off white solid. LC-MS: 328 (M+H)+.

후처리

  1. temperatureAfter cooling
  2. customthe crude residue was purified by flash column chromatography (100-200 mesh silica, eluting with 50% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-90f5325a094f469d8076bf140a76a38e
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09199938B2

연결된 노트

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