1-萘甲酸 → (2-甲基-1H-吲哚-3-基)-1-萘基甲酮

HRID 55931

反应方程式

HRID 55931 反应方程式
[C:1]1([C:11]([C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[NH:15][CH:14]=2)=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C[Mg+].[Br-].[C:25]1(C(O)=O)C2C(=CC=CC=2)C=CC=1>C(OCC)C.S(Cl)(Cl)=O>[CH3:25][C:14]1[NH:15][C:16]2[C:21]([C:13]=1[C:11]([C:1]1[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=1)=[O:12])=[CH:20][CH:19]=[CH:18][CH:17]=2

参与物

6

反应物 3

HCID 68471-萘甲酸HCID 103558253-(1-萘甲酰基)吲哚HCID 178418689HCID 178418689，化合物

产物 1

HCID 11778684(2-甲基-1H-吲哚-3-基)-1-萘基甲酮收率 1,133.2%

试剂、催化剂与溶剂 2

HCID 3283乙醚溶剂HCID 24386氯化亚砜溶剂

反应条件

温度
0 °C

实验过程

2-Methylindole 1 (10 g, 76 3 mmol) was dissolved in diethylether (100 ml) under nitrogen atmosphere and cooled to 0° C. MeMgBr (3M) solution (26.7 ml, 80.15 mmol) was added dropwise and allowed to stir at room temperature for 3 hours. In the meantime, 1-naphthoic acid (13.13 g, 76 3 mmol) was dissolved in thionyl chloride (50 ml) and refluxed for 90 min, then the solvent was removed under vacuo and the residue was dissolved in diethylether (50 ml). The resulting solution was added dropwise to the indole reaction mixture at 0° C. and then allowed to stir at room temperature for 2 hours. A solution of ammonium chloride (200 ml) was added to the reaction mixture and the resulting mixture was stirred at room temperature overnight. The solid that was formed was collected by filtration, washed with water and hexane then dried in a dessicator over phosphorous pentoxide to give 9.7 g (45%) (2-methyl-1H-indol-3-yl)(naphthalen-1-yl) methanone 2 as a cream solid.

后处理

  1. temperaturerefluxed for 90 min
  2. customthe solvent was removed under vacuo
  3. dissolutionthe residue was dissolved in diethylether (50 ml)
  4. additionThe resulting solution was added dropwise to the indole reaction mixture at 0° C.
  5. stirringto stir at room temperature for 2 hours
  6. additionA solution of ammonium chloride (200 ml) was added to the reaction mixture
  7. stirringthe resulting mixture was stirred at room temperature overnight
  8. customThe solid that was formed
  9. filtrationwas collected by filtration
  10. washwashed with water and hexane
  11. dry with materialthen dried in a dessicator over phosphorous pentoxide

来源与证据

ORD记录
ord-ba58fb38ded749dba9c0682a8cc39af9
来源数据集
uspto-grants-2016_09
专利号
US09434687B2

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