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Methanesulfonic Acid → 6-Methoxy-4-(5,6,5'-trimethyl-[2,2']bipyridin-3-yloxy)-quinolin-7-ol

HRID 229078
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HRID 229078 반응식
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[C:21]([C:28]4[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][N:29]=4)=[N:22][C:23]([CH3:27])=[C:24]([CH3:26])[CH:25]=3)=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:35][CH3:36])C1C=CC=CC=1.CS(O)(=O)=O>FC(F)(F)C(O)=O>[CH3:36][O:35][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:9]=1[OH:8])[N:16]=[CH:15][CH:14]=[C:13]2[O:19][C:20]1[C:21]([C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][N:29]=2)=[N:22][C:23]([CH3:27])=[C:24]([CH3:26])[CH:25]=1
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참가 물질

4

반응물 2

HCID 6395Methanesulfonic AcidHCID 577563763-(7-Benzyloxy-6-methoxy-quinolin-4-yloxy)-5,6,5'-trimethyl-[2,2']bipyridine2회

생성물 1

HCID 1361316196-Methoxy-4-(5,6,5'-trimethyl-[2,2']bipyridin-3-yloxy)-quinolin-7-ol수율 88.3%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

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온도
70 °C

실험 절차

3-(7-Benzyloxy-6-methoxy-quinolin-4-yloxy)-5,6,5′-trimethyl-[2,2′]bipyridine (compound 452) (500 mg) was dissolved in trifluoroacetic acid (5 ml) to prepare a solution. Methanesulfonic acid (0.5 ml) was added to the solution, and the mixture was stirred at 70° C. for 1.5 hr. The reaction solution was cooled to room temperature, and the solvent was removed by distillation under the reduced pressure. An aqueous sodium hydrogencarbonate solution was then added to the residue, and the mixture was extracted with chloroform. The chloroform layer was washed with saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using chloroform-methanol to give the title compound (358 mg, yield 88%).

후처리

  1. customto prepare a solution
  2. temperatureThe reaction solution was cooled to room temperature
  3. customthe solvent was removed by distillation under the reduced pressure
  4. additionAn aqueous sodium hydrogencarbonate solution was then added to the residue
  5. extractionthe mixture was extracted with chloroform
  6. washThe chloroform layer was washed with saturated brine
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. customThe solvent was removed by distillation under the reduced pressure
  9. customthe residue was purified by thin layer chromatography

출처 및 근거

ORD 기록
ord-2b7743f2952646a7b420c0f6ad91d9fd
출처 데이터셋
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07560558B2

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