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Diisopropyl Ether → 2-Methoxy-4-methylquinoline

HRID 2274756
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HRID 2274756 반응식
Br[CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5]([O:13][CH3:14])[CH:4]=1.COC1C=CC2N=CC=C([C@@H](O)[C@H]3N4C[C@H](C=C)[C@@H](CC4)C3)C=2C=1.C(OC(C)C)(C)C>C(#N)C>[CH3:14][O:13][C:5]1[CH:4]=[C:3]([CH3:2])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 7914Diisopropyl EtherHCID 3034034QuinineHCID 23001499HCID 23001499, 화합물

생성물 1

HCID 847962-Methoxy-4-methylquinoline

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
70 °C

실험 절차

The 4-(bromomethyl)-2-methoxyquinoline obtained in Step 2 was dissolved in 7 mL of acetonitrile, and then 0.5 g (1.54 mmol) of quinine was added, and stirred for 2 hours while heated at 70° C. After stirring was completed, the solution was cooled to a normal temperature, and 20 mL of diisopropyl ether was added. Then, the solution was filtered under reduced pressure to separate a solid precipitated in the reaction solution. The resultant residual solid was washed with a mixed solvent of 5 mL of chloroform and 15 mL of diisopropyl ether. After washing, the solid was dried under reduced pressure to obtain 0.82 g of the target compound, 2-methoxy-4-methyl quinoline quininium bromide. The melting point was 181° C. to 191° C. (degradation). M+496 was confirmed by LCMS.

후처리

  1. stirringAfter stirring
  2. additionwas added
  3. filtrationThen, the solution was filtered under reduced pressure
  4. customto separate a solid
  5. customprecipitated in the reaction solution
  6. washThe resultant residual solid was washed with a mixed solvent of 5 mL of chloroform and 15 mL of diisopropyl ether
  7. washAfter washing
  8. customthe solid was dried under reduced pressure

출처 및 근거

ORD 기록
ord-a0e7f684d3fe4729a97e3b769d6011da
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09126995B2

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