2-(4-Fluorobenzyl)acetoacetic acid ethyl ester → HCID 68780079, 화합물

HRID 2266492노트

반응식

HRID 2266492 반응식
[CH3:1][O:2][C:3](=[O:14])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([NH2:13])[CH:7]=1.C([O:17][C:18](=O)[CH:19]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)[C:20](=O)[CH3:21])C>O>[CH3:1][O:2][C:3](=[O:14])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]2[C:7]=1[C:20]([CH3:21])=[C:19]([CH2:23][C:24]1[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=1)[C:18](=[O:17])[NH:13]2.[CH3:1][O:2][C:3](=[O:14])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]2[C:7]=1[C:18](=[O:17])[C:19]([CH2:23][C:24]1[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=1)=[C:20]([CH3:21])[NH:13]2

참가 물질

5

반응물 2

HCID 27695652-(4-Fluorobenzyl)acetoacetic acid ethyl esterHCID 66717604Methyl 2-(3-amino-4-chlorophenoxy)acetate

생성물 2

HCID 68780079HCID 68780079, 화합물HCID 68787407HCID 68787407, 화합물

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

A mixture of (3-amino-4-chlorophenoxy)acetic acid methyl ester (1.5 g), 2-(4-fluorobenzyl)-3-oxobutyric acid ethyl ester (1.7 g) and polyphosphoric acid (15 g) was heated at 100° C. for 3 hours. The mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate. The combined extracts were washed with water and saturated aqueous sodium chloride solution and then dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel, eluting with a mixture of ethyl acetate and cyclohexane (3:7 by volume) to afford [8-chloro-3-(4-fluorobenzyl)-4-methyl-2-oxo-1,2-dihydroquinolin-5-yloxy]acetic acid methyl ester as a yellow-brown solid, 0.13 g and [8-chloro-3-(4-fluorobenzyl)-2-methyl-4-oxo-1,4-dihydroquinolin-5-yloxy]acetic acid methyl ester as a brown oil, 0.21 g.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed with water and saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue purified by column chromatography on silica gel
  7. washeluting with a mixture of ethyl acetate and cyclohexane (3:7 by volume)

출처 및 근거

ORD 기록
ord-fdbfb1306df54530816d303ce07253fb
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07858640B2

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