1，2-二甲基肼 → 3-Cyano-1-(4-dimethylamino-benzoyl)-pyrrolo[1,2-a]quinoline

HRID 720430笔记

反应方程式

HRID 720430 反应方程式
[C:1]([C:3]1[CH:4]=[C:5]([C:16](=[O:24])[C:17]2[CH:22]=[CH:21][C:20](F)=[CH:19][CH:18]=2)[N:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8][C:7]=12)#[N:2].CNNC.[CH3:29][N:30](C=O)[CH3:31]>O>[C:1]([C:3]1[CH:4]=[C:5]([C:16](=[O:24])[C:17]2[CH:22]=[CH:21][C:20]([N:30]([CH3:31])[CH3:29])=[CH:19][CH:18]=2)[N:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8][C:7]=12)#[N:2]

参与物

5

反应物 3

HCID 13221，2-二甲基肼HCID 6228N,N-二甲基甲酰胺HCID 102676303-Cyano (4-fluoro-benzoyl)-pyrrolo[1,2-a]quinoline

产物 1

HCID 218921233-Cyano-1-(4-dimethylamino-benzoyl)-pyrrolo[1,2-a]quinoline收率 25%

试剂、催化剂与溶剂 1

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂

实验过程

A solution of 3-cyano-1-[4-fluoro-benzoyl]-pyrrolo[1,2-a]quinoline (56 mg, 0.18 mmol) and dimethylhydrazine (118 mg, 1.96 mmol) in DMF (5 mL) was refluxed for 24 h. It was diluted with water (50 mL) and extracted with EtOAc (3×20 mL). The combined organic layers were dried, concentrated and the residue was purified by column chromatography (EtOAc/Hexane 6:1) to give 15 mg (25%) of the title compound. 1H NMR (CDCl3): 8.11–8.05–7.95 (m, 3H), 7.82–7.78 (m, 2H), 7.63–7.42 (m, 4H), 7.31 (s, 1H), 6.75 (d, J=9.30 Hz, 2H), 3.14 (s, 6H). MS, 340 (M+1).

后处理

  1. extractionextracted with EtOAc (3×20 mL)
  2. customThe combined organic layers were dried
  3. concentrationconcentrated
  4. customthe residue was purified by column chromatography (EtOAc/Hexane 6:1)

来源与证据

ORD记录
ord-5009080523824638a9d9dbb27028aedd
来源数据集
uspto-grants-2006_11
专利号
US07135480B2

反应笔记

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