乙氧基喹啉 → 2,2,4-三甲基-1,2-二氢喹啉-6-醇

HRID 25795

反应方程式

HRID 25795 反应方程式
C([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([CH3:15])([CH3:14])[CH:8]=[C:7]2[CH3:16])C.B(Br)(Br)Br>ClCCl>[CH3:14][C:9]1([CH3:15])[CH:8]=[C:7]([CH3:16])[C:6]2[C:11](=[CH:12][CH:13]=[C:4]([OH:3])[CH:5]=2)[NH:10]1

参与物

4

反应物 2

HCID 3293乙氧基喹啉HCID 25134三溴化硼2 次

产物 1

HCID 5997992,2,4-三甲基-1,2-二氢喹啉-6-醇收率 45.9%

试剂、催化剂与溶剂 1

HCID 6344二氯甲烷溶剂

实验过程

A solution of 31 g of 6-ethoxy-2,2,4-trimethyl-1,2-dihydroquinoline in 300 mL of dichloromethane was treated with 30 mL of boron tribromide dropwise at −78° C. After the addition of boron tribromide, the cooling bath was removed and the reaction mixture was allowed to warm to room temperature. The resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was then poured into crushed ice and the pH was adjusted to 9 with sodium bicarbonate. The product was the extracted into EtOAc. The organic solution was washed with water and brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by filtering through a short plug of silica gel eluting with 25% EtOAc in hexanes solution to give 12.4 g of 2,2,4-trimethyl-1,2-dihydroquinolin-6-ol as a light brown solid.

后处理

  1. customthe cooling bath was removed
  2. additionThe reaction mixture was then poured
  3. custominto crushed ice
  4. extractionextracted into EtOAc
  5. washThe organic solution was washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified
  10. filtrationby filtering through a short plug of silica gel eluting with 25% EtOAc in hexanes solution

来源与证据

ORD记录
ord-b788bc3ae1e342adb325965bd12b86b8
来源数据集
uspto-grants-2005_02
专利号
US06858627B2

关联笔记

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