1,2-二氯乙烷 → 喹啉

HRID 53654

反应方程式

HRID 53654 反应方程式
[CH:1]1[CH:6]=[C:5]2[CH:7]=[CH:8][C:9](C(O)=O)=[N:10][C:4]2=[CH:3][CH:2]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[N:10]1[C:4]2[C:5](=[CH:6][CH:1]=[CH:2][CH:3]=2)[CH:7]=[CH:8][CH:9]=1

参与物

5

反应物 3

HCID 111,2-二氯乙烷HCID 7124喹哪啶酸HCID 757711-羟基苯并三唑(HOBT)

产物 1

HCID 7047喹啉收率 319.5%

试剂、催化剂与溶剂 1

HCID 6228N,N-二甲基甲酰胺溶剂2 次

反应条件

温度
0 °C

实验过程

A 100 ml RBF equipped with magnetic stir bar and N2 inlet was charged with 356 mg (2.06 mmol, 1 eq) 2-quinaldic acid in 10 ml dry DMF. The solution was cooled to 0° C. and 415 mg (3.07 mmol, 1.5 eq) HOBt was added followed by 415 mg EDC (2.16 mmol, 1.05 eq). The reaction was stirred 2 hours at 0° C. when 1.1 g (2.06 mmol, 1 eq) of free asparagine amine in 10 ml dry DMF was added. The reaction was stirred at 0° C. for 2 hours then room temperature overnight. The reaction was poured into sat. bicarb and extracted with 2×65 mL ethyl acetate. The combined organics were washed with 5% aq. citric acid, brine, dried and concentrated to 1.4 g crude foam. Purification by flash chromatography on silica gel (100% ethyl acetate) yielded 850 mg (61%) of quinoline adduct.

后处理

  1. customA 100 ml RBF equipped with magnetic stir bar and N2 inlet
  2. additionwas added
  3. customroom temperature overnight
  4. additionThe reaction was poured into sat. bicarb
  5. extractionextracted with 2×65 mL ethyl acetate
  6. washThe combined organics were washed with 5% aq. citric acid, brine
  7. customdried
  8. concentrationconcentrated to 1.4 g crude foam
  9. customPurification by flash chromatography on silica gel (100% ethyl acetate)

来源与证据

ORD记录
ord-2418f6fa7a6540388b5cd366afeeca75
来源数据集
uspto-grants-1997_04
专利号
US05620977

关联笔记

加载中…