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

HRID 1503153ノート

反応式

HRID 1503153 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
230 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-175d7e59ef24468c90859bbaed6b54f8
出典データセット
uspto-grants-2015_12
特許番号
US09212144B2

反応ノート

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