8-Methoxyquinoline → 8-Methoxy-2-(2-methoxyphenyl)quinoline

HRID 1893143

반응식

HRID 1893143 반응식
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[CH:10][CH:9]=[CH:8]2.[Li][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH3:21].C(OCC)(=O)C.CCCCCC>C(OCC)C.[O-2].[O-2].[Mn+4]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH3:21])[CH:9]=[CH:8]2

참가 물질

6

반응물 3

HCID 703108-MethoxyquinolineHCID 21226206Ethyl acetate hexaneHCID 178506687HCID 178506687, 화합물

생성물 1

HCID 672565848-Methoxy-2-(2-methoxyphenyl)quinoline

시약·촉매·용매 2

HCID 178418406HCID 178418406, 화합물촉매HCID 3283Diethyl Ether용매2회

실험 절차

A solution of 8-methoxyquinoline (5.54 g, 34.8 mmol, 1.0 eq) in 55 ml diethyl ether was slowly dropped (within about 30 min) into a solution of o-lithioanisole (4.37 g, 38.4 mmol, 1.1 eq) in 55 ml diethyl ether (each 55 mL). A yellow green fluorescing solution was formed. At the conclusion of the addition, stirring was continued at room temperature for a further 2 hours, after which no more educt could be detected by thin layer chromatography. During the reaction, the color of the reaction mixture changed from fluorescent yellow to green to green-brown. The reaction mixture was worked up by adding it to ice and subsequent extraction with diethyl ether (3×40 ml). The combined organic phases (yellow) were dried over MgSO4 and the solvent was removed in a rotary evaporator. The residue was dissolved in 200 ml dichloromethane and stirred with ca. 40 equivalents of activated manganese dioxide (Merck) until the thin layer chromatographic control (ethyl acetate/hexane=4/6) showed that all of the crude product had reacted. The manganese dioxide was filtered off and the solvent removed in the rotary evaporator. The product was dried under vacuum.

후처리

  1. customA yellow green fluorescing solution was formed
  2. additionAt the conclusion of the addition
  3. customDuring the reaction
  4. additionby adding it
  5. extractionto ice and subsequent extraction with diethyl ether (3×40 ml)
  6. dry with materialThe combined organic phases (yellow) were dried over MgSO4
  7. customthe solvent was removed in a rotary evaporator
  8. dissolutionThe residue was dissolved in 200 ml dichloromethane
  9. customhad reacted
  10. filtrationThe manganese dioxide was filtered off
  11. customthe solvent removed in the rotary evaporator
  12. customThe product was dried under vacuum

출처 및 근거

ORD 기록
ord-14b7c19316fd4cf2abc8f9176a91023f
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08513177B2

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