Methyl iodide → 7-Methoxyquinoline

HRID 656850노트

반응식

HRID 656850 반응식
[H-].[Na+].[N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([OH:13])[CH:11]=2)[CH:6]=[CH:5][CH:4]=1.[CH3:14]I>CN(C=O)C>[CH3:14][O:13][C:10]1[CH:11]=[C:12]2[C:7]([CH:6]=[CH:5][CH:4]=[N:3]2)=[CH:8][CH:9]=1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 1354268667-Hydroxyquinoline

생성물 1

HCID 786667-Methoxyquinoline수율 99.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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온도
0 °C

실험 절차

A suspension of NaH (3.3 g; 137.93 mmol) in anhydrous DMF (160 ml) was cooled to 0° C. with stirring under argon. 7-Quinolinol (8 g; 55.17 mmol) dissolved in anhydrous DMF (320 ml) was added and the mixture was stirred at 0° C. under argon for 1 h. The mixture was then allowed to warm to rt and MeI (7.8 ml; 55.17 mmol) was added and the reaction was stirred for 1 h. Ice water was then added cautiously and the resulting mixture extracted with EtOAc (3×500 ml). The organic layer from this extraction was then washed with water (400 ml) and brine (400 ml). The resulting organic layer was dried with MgSO4 and solvents removed to afford the desired compound (8.76 g; 99%)

후처리

  1. additionwas added
  2. stirringthe mixture was stirred at 0° C. under argon for 1 h
  3. temperatureto warm to rt
  4. stirringthe reaction was stirred for 1 h
  5. extractionthe resulting mixture extracted with EtOAc (3×500 ml)
  6. extractionThe organic layer from this extraction
  7. washwas then washed with water (400 ml) and brine (400 ml)
  8. dry with materialThe resulting organic layer was dried with MgSO4 and solvents
  9. customremoved

출처 및 근거

ORD 기록
ord-2a9506de2aac4e4f8738396daa2562aa
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071592B2

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