Potassium Carbonate → Methyl 4-methoxy-3-[(5-nitropyridin-2-yl)oxy]benzoate

HRID 1800430노트

반응식

HRID 1800430 반응식
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6].Cl[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][N:16]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH3:13][O:12][C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=1[O:1][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][N:16]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 4056967Methyl 3-hydroxy-4-methoxybenzoate

생성물 1

HCID 68418010Methyl 4-methoxy-3-[(5-nitropyridin-2-yl)oxy]benzoate수율 119.8%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

To a solution of methyl 3-hydroxy-4-methoxybenzoate (4.87 g, 26.7 mmol) and 2-chloro-5-nitropyridine (4.24 g, 26.7 mmol) in N,N-dimethylformamide (100 mL) was added potassium carbonate (8.13 g, 58.8 mmol), and the mixture was stirred at 60° C. for 14 hr. The reaction solution was cooled to room temperature, diluted with water, and extracted with a mixed solvent (1:1, 100 mL) of ethyl acetate and hexane. The combined organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (9.73 g) as an orange syrup substance.

후처리

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionextracted with a mixed solvent (1:1, 100 mL) of ethyl acetate and hexane
  3. washThe combined organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe insoluble material was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-9a25c3ca132d450485b78f1772b23d1b
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08344135B2

반응 노트

불러오는 중…