Morpholine → 6-Chloro-2-morpholin-4-yl-4-phenyl-quinoline-3-carboxylic acid ethyl ester

HRID 1497057노트

반응식

HRID 1497057 반응식
[CH2:1]([O:3][C:4]([C:6]1[C:7](Cl)=[N:8][C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:13][C:12]([Cl:22])=[CH:11][CH:10]=2)=[O:5])[CH3:2].[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1>O>[CH2:1]([O:3][C:4]([C:6]1[C:7]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)=[N:8][C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:13][C:12]([Cl:22])=[CH:11][CH:10]=2)=[O:5])[CH3:2]

참가 물질

4

반응물 2

HCID 8083MorpholineHCID 1714247Ethyl 2,6-dichloro-4-phenylquinoline-3-carboxylate

생성물 1

HCID 866829316-Chloro-2-morpholin-4-yl-4-phenyl-quinoline-3-carboxylic acid ethyl ester수율 57%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
150 °C

실험 절차

To a stirred solution of 2,6-dichloro-4-phenyl-quinoline-3-carboxylic acid ethyl ester (prepared as described in example 11 step B, 100 mg, 0.29 mmol) in a sealed tube was added morpholine (0.038 ml, 0.43 mmol). Then the mixture was stirred at 150° C. for 3 h. After cooling, this reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo to afford a crude residue which was purified by flash column chromatography (100-200 mesh silica, eluting with 10% ethyl acetate in hexane) to give 6-chloro-2-morpholin-4-yl-4-phenyl-quinoline-3-carboxylic acid ethyl ester (65 mg, 57%) as pale yellow solid. LC-MS: 397 (M+H)+.

후처리

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto afford a crude residue which
  7. customwas purified by flash column chromatography (100-200 mesh silica, eluting with 10% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-61d0afad1fcc42329a8658502939fb12
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09199938B2

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