Sulfuric Acid → 6-Chloro-8-methoxyquinoline

HRID 2048067노트

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HRID 2048067 반응식
S(=O)(=O)(O)O.[ClH:6].Cl[C:8]1[CH:9]=[C:10]([NH2:16])[C:11](=[CH:14][CH:15]=1)[O:12][CH3:13].[Na+].[N+]([C:21]1C=C(S([O-])(=O)=O)C=[CH:25][CH:26]=1)([O-])=O.B(O)(O)O.[OH-].[Na+]>O.C(Cl)Cl.OCC(CO)O>[Cl:6][C:15]1[CH:8]=[C:9]2[C:10](=[C:11]([O:12][CH3:13])[CH:14]=1)[N:16]=[CH:25][CH:26]=[CH:21]2

참가 물질

9

반응물 5

HCID 1118Sulfuric AcidHCID 7628Boric AcidHCID 14798Sodium HydroxideHCID 31389Sodium 3-nitrobenzenesulfonateHCID 77957Benzenamine, 5-chloro-2-methoxy-, hydrochloride

생성물 1

HCID 580424696-Chloro-8-methoxyquinoline수율 58%

시약·촉매·용매 3

HCID 753Glycerol용매HCID 962Water용매HCID 6344Dichloromethane용매

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온도
140 °C

실험 절차

Concentrated sulphuric acid (40 mL) was added to a mixture of 4-chloro-2-anisidine hydrochloride (20 g, 127 mmol), m-nitrobenzene sulfonic acid sodium salt (42.4 g, 190 mmol), boric acid (10 g, 161.8 mmol), ferrous sulfate (6.0 g, 21.5 mmol) and glycerol (400 mL) at room temperature. The mixture was heated at 140° C. for 30 minutes. The reaction mixture was diluted with water (500 mL) and the pH adjusted to 10 with 10% aqueous sodium hydroxide solution. DCM (1 L) was added, stirred for 30 minutes, filtered through celite and the layers separated. The aqueous layer was extracted with DCM (2×500 mL) and the combined organic layers were washed with brine (500 mL), dried over anhydrous sodium sulfate and concentrated in vacuo. The resulting crude product was purified with silica gel chromatography eluting with 20% EtOAc in petroleum ether to yield the title compound as a liquid (14.2 g, 58%):

후처리

  1. filtrationfiltered through celite
  2. customthe layers separated
  3. extractionThe aqueous layer was extracted with DCM (2×500 mL)
  4. washthe combined organic layers were washed with brine (500 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe resulting crude product was purified with silica gel chromatography
  8. washeluting with 20% EtOAc in petroleum ether

출처 및 근거

ORD 기록
ord-6b80d4b4f3ca4b5f941a386492eabbba
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08592629B2

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