Sodium Iodide → Methyl 8-(dodecyloxy)quinoline-2-carboxylate

HRID 252477노트

반응식

HRID 252477 반응식
[CH2:1](Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[Na+].[I-].[H-].[Na+].[CH3:18][O:19][C:20]([C:22]1[CH:31]=[CH:30][C:29]2[C:24](=[C:25]([OH:32])[CH:26]=[CH:27][CH:28]=2)[N:23]=1)=[O:21]>CN(C=O)C.C(Cl)Cl>[CH3:18][O:19][C:20]([C:22]1[CH:31]=[CH:30][C:29]2[C:24](=[C:25]([O:32][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH:26]=[CH:27][CH:28]=2)[N:23]=1)=[O:21]

참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 89191-BromododecaneHCID 24758Sodium hydrideHCID 12336161Methyl 8-Hydroxyquinoline-2-Carboxylate

생성물 1

HCID 66872454Methyl 8-(dodecyloxy)quinoline-2-carboxylate수율 14%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

In a first step, dodecyl bromide (767 μL, 3.2 mmol), NaI (478 mg, 3.2 mmol) and NaH (76 mg, 3.2 mmol) were added to a solution of 8-hydroxyl-quinoline-2-carboxylic acid methyl ester (2.11 mmol) stirring in DMF (dry, 10 mL), and the red reaction was allowed to stir overnight. The crude material resulting from removal of solvents by rotary evaporation was taken into DCM, washed with water, dried over Na2SO4, and filtered. The resulting solution was evaporated to dryness and the desired intermediate, 8-dodecyloxy-quinoline-2-carboxylic acid methyl ester, was obtained by HPLC (isocratic, 75% acetonitrile, 25% water) yielding 169 mg (about 14% yield). This intermediate was in turn deprotected using LiOH in THF/H2O as described in the method of Example 336 to yield the title compound, which was utilized further without additional purification or characterization.

후처리

  1. customthe red reaction
  2. customThe crude material resulting from removal of solvents by rotary evaporation
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customThe resulting solution was evaporated to dryness

출처 및 근거

ORD 기록
ord-ebd5ed555b5d43279656f61d7c912a24
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07868135B2

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