海萝胶 → 1-(8-Hydroxy-5-methyl-7-quinolinyl)ethanone

HRID 1192560

反应方程式

HRID 1192560 反应方程式
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[Cl-].[Cl-].[Cl-].[Al+3].[C:17](Cl)(=[O:19])[CH3:18].Cl.[OH-].[Na+]>O.ClCCl>[OH:12][C:9]1[C:10]([C:17](=[O:19])[CH3:18])=[CH:11][C:2]([CH3:1])=[C:3]2[C:8]=1[N:7]=[CH:6][CH:5]=[CH:4]2

参与物

8

反应物 5

HCID 313海萝胶HCID 6367乙酰氯HCID 14798二甲基对苯二胺二盐酸HCID 712088-羟基-5-甲基喹啉HCID 6451240三氯化铝

产物 1

HCID 190434591-(8-Hydroxy-5-methyl-7-quinolinyl)ethanone

试剂、催化剂与溶剂 2

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂2 次HCID 6344二氯甲烷溶剂

反应条件

温度
0 °C

实验过程

A mixture of 5-methylquinolin-8-ol (5.91 g, 37.1 mmol, from ChemBridge), aluminum trichloride (20.00 g, 150.0 mmol), and acetyl chloride (12.1 mL, 170 mmol) was stirred at 0° C. for 4 hours, then heated at 130° C. for 12 hours, cooled, and decomposed with water (39 mL) (caution! with external ice-cooling if necessary) and conc. HCl (13 mL). The precipitate was filtered, and dried under reduced pressure. The solid obtained was then dissolved in 50 mL of water. To the solution was added 100 mL of dichloromethane. The mixture was cooled with an ice bath and the pH adjusted to 4 with slow addition of 20% NaOH. The layers were separated and the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with water, brine and dried over sodium sulfate. The suspension was filtered through a plug of cotton and concentrated to dryness. The residue was used directly in the next step (5.8 g, 78%). LCMS calculated for C12H12NO2 (M+H)+: m/z=202.1; Found: 202.0.

后处理

  1. temperatureheated at 130° C. for 12 hours
  2. temperaturecooled
  3. filtrationThe precipitate was filtered
  4. customdried under reduced pressure
  5. customThe solid obtained
  6. temperatureThe mixture was cooled with an ice bath
  7. customThe layers were separated
  8. extractionthe aqueous layer was extracted with dichloromethane
  9. washThe combined organic layers were washed with water, brine
  10. dry with materialdried over sodium sulfate
  11. filtrationThe suspension was filtered through a plug of cotton
  12. concentrationconcentrated to dryness

来源与证据

ORD记录
ord-fda3c65bbef748bcb621dd751cbffa39
来源数据集
uspto-grants-2014_03
专利号
US08680108B2

关联笔记

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