Methanol → methyl2-(7-amino-4-methyl-2-oxo-2H-chromen-3-yl)acetate

HRID 2369748

반응식

HRID 2369748 반응식
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:17])=[C:7]([CH2:13][C:14]([OH:16])=[O:15])[C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.[CH3:18]O>OS(O)(=O)=O>[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:17])=[C:7]([CH2:13][C:14]([O:16][CH3:18])=[O:15])[C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 887MethanolHCID 1293677-Amino-4-methylcoumarin-3-acetic acid

생성물 1

HCID 86668467methyl2-(7-amino-4-methyl-2-oxo-2H-chromen-3-yl)acetate수율 75%

시약·촉매·용매 1

HCID 1118Sulfuric Acid촉매

반응 조건

온도
120 °C

실험 절차

7-Amino-4-methyl-3-coumarinylacetic acid (43.1 mg, 0.18 mmol) was dissolved in MeOH (40 ml). H2SO4 (5 drops) was added, and the reaction mixture was heated to 120° C. and stirred. After 4 hr, the disappearance of the starting materials was confirmed, and the reaction mixture was cooled to room temperature. The reaction mixture was concentrated to ⅓ and the mixture was neutralized with aqueous saturated NaHCO3 solution. The reaction mixture was extracted with BuOH, and the organic layer was concentrated. The residue was purified by silica gel column chromatography (eluate: hexane:EtOAc=1:2) to give the object compound (34.4 mg, 0.14 mmol, 75%).

후처리

  1. temperaturethe reaction mixture was cooled to room temperature
  2. concentrationThe reaction mixture was concentrated
  3. extractionThe reaction mixture was extracted with BuOH
  4. concentrationthe organic layer was concentrated
  5. customThe residue was purified by silica gel column chromatography (eluate: hexane:EtOAc=1:2)

출처 및 근거

ORD 기록
ord-3954169c5b93459d91dc616754cf0221
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08709721B2

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