Sodium Sulfate → 3-Nitro-7-(5-ethyl-2-pyridylmethoxy)quinoline

HRID 1938343노트

반응식

HRID 1938343 반응식
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([OH:14])[CH:8]=2)([O-:3])=[O:2].[H-].[Na+].[CH2:17]([C:19]1[CH:20]=[CH:21][C:22]([CH2:25]Cl)=[N:23][CH:24]=1)[CH3:18].S([O-])([O-])(=O)=O.[Na+].[Na+]>CN(C=O)C.C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([O:14][CH2:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:17][CH3:18])=[CH:24][N:23]=1)[CH:8]=2)([O-:3])=[O:2]

참가 물질

7

반응물 4

HCID 24436Sodium SulfateHCID 24758Sodium hydrideHCID 157171792-(Chloromethyl)-5-ethylpyridineHCID 1357342933-Nitroquinolin-7-ol

생성물 1

HCID 214692903-Nitro-7-(5-ethyl-2-pyridylmethoxy)quinoline수율 43.5%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

In DMF (9 mL) was dissolved 3-nitro-7-hydroxyquinoline (1.0 g, 5.28 mmol.). Sodium hydride (210 mg, 5.28 mmol.) and 5-ethyl-2-(chloromethyl)pyridine (818 mg, 5.28 mmol.) were added to the resulting solution under chilling with ice. The mixture was stirred overnight at room temperature. After the completion of reaction was confirmed, ethyl acetate and aqueous sodium sulfate were added. The ethyl acetate portion was recovered, washed with water, and dried over sodium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (chloroform to chloroform/methanol=50/1), to give 710 mg of the desired compound as a yellowish white crystalline product (yield 44%).

후처리

  1. temperatureunder chilling with ice
  2. customAfter the completion of reaction
  3. customThe ethyl acetate portion was recovered
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (chloroform to chloroform/methanol=50/1)

출처 및 근거

ORD 기록
ord-2ba26b8e29a646ea886de1658e5cc04a
출처 데이터셋
uspto-grants-1997_12
특허 번호
US05693651

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