Acetamide → N-(6-methylquinolin-2-yl)acetamide

HRID 1503153노트

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HRID 1503153 반응식
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:12])[CH:8]=2)[N:3]=1.[C:13]([NH2:16])(=[O:15])[CH3:14].C([O-])([O-])=O.[K+].[K+]>O>[C:13]([NH:16][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:12])[CH:8]=2)[N:3]=1)(=[O:15])[CH3:14]

참가 물질

5

반응물 3

HCID 178AcetamideHCID 11430Potassium CarbonateHCID 779742-Chloro-6-methylquinoline

생성물 1

HCID 11458305N-(6-methylquinolin-2-yl)acetamide수율 74%

시약·촉매·용매 1

HCID 962Water용매

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온도
230 °C

실험 절차

Chloride 44 (0.300 g, 1.69 mmol) was diluted with molten anhydrous acetamide (8 g, 135 mmol), and K2CO3 (1.17 g, 8.45 mmol) was added. The mixture was heated in a sand bath, at reflux (˜230° C.) for 16 h. The mixture was cooled, poured into H2O (120 mL) and extracted with EtOAc (4×30 mL). The organic layers were washed with H2O (3×100 mL) and sat. aq. NaCl (50 mL) and dried over anhydrous sodium sulfate and concentrated. Purification of the residue by flash column chromatography (SiO2), eluting with a gradient of 10% EtOAc in CH2Cl2 to 30% EtOAc in CH2Cl2 afforded the desired compound as a white solid (0.250 g, 74%). 1H NMR chemical shifts for this compound are consistent with those reported in the literature. 1H-NMR (500 MHz; CDCl3): δ 8.36 (br d, J=8.6 Hz, 1 H), 8.27 (br s, 1 H), 8.09 (d, J=8.9 Hz, 1 H), 7.70 (d, J=8.6 Hz, 1 H), 7.55 (s, 1 H), 7.50 (dd, J=8.6, 1.9 Hz, 1 H), 2.51 (s, 3 H), 2.24 (s, 3 H).

후처리

  1. additionwas added
  2. temperatureThe mixture was heated in a sand bath
  3. temperatureThe mixture was cooled
  4. extractionextracted with EtOAc (4×30 mL)
  5. washThe organic layers were washed with H2O (3×100 mL) and sat. aq. NaCl (50 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customPurification of the residue by flash column chromatography (SiO2)
  9. washeluting with a gradient of 10% EtOAc in CH2Cl2 to 30% EtOAc in CH2Cl2

출처 및 근거

ORD 기록
ord-175d7e59ef24468c90859bbaed6b54f8
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09212144B2

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