聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯] → 5-Bromo-4-[2-(dimethylamino)ethenyl]-2-methoxy-3-nitropyridine

HRID 930833笔记

反应方程式

HRID 930833 反应方程式
[Br:1][C:2]1[C:3]([CH3:13])=[C:4]([N+:10]([O-:12])=[O:11])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.C[O-].[Li+].CO[CH:19](OC)[N:20]([CH3:22])[CH3:21].O>CN(C)C=O>[Br:1][C:2]1[C:3](/[CH:13]=[CH:19]/[N:20]([CH3:22])[CH3:21])=[C:4]([N+:10]([O-:12])=[O:11])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1

参与物

6

反应物 4

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]HCID 78373N,N-二甲基甲酰胺二甲基缩醛HCID 4177230甲醇锂HCID 407869095-溴-2-甲氧基-4-甲基-3-硝基吡啶

产物 1

HCID 578831255-Bromo-4-[2-(dimethylamino)ethenyl]-2-methoxy-3-nitropyridine收率 76%

试剂、催化剂与溶剂 1

HCID 6228N,N-二甲基甲酰胺溶剂

反应条件

温度
100 °C

实验过程

5-Bromo-2-methoxy-4-methyl-3-nitropyridine (15.0 g, 60.7 mmol) was dissolved in dimethylformamide (300 mL), and lithium methanolate (6.07 mL, 6.07 mmol, 1 M) was added. The reaction mixture was heated to 100° C. To this mixture was added 1,1-dimethoxy-N,N-dimethylmethanamine (64.5 mL, 486 mmol) over 10 minutes. The reaction mixture was stirred at 95° C. for 16 hours. The reaction mixture was cooled to room temperature and water was added carefully (300 mL, exothermic). The resulting precipitate was collected by vacuum filtration, washed with water, and dried to provide the title compound (13.9 g, 45.9 mmol, 76% yield).

后处理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe resulting precipitate was collected by vacuum filtration
  3. washwashed with water
  4. customdried

来源与证据

ORD记录
ord-cf816a7051ad45f6a98ca1e28e58e798
来源数据集
uspto-grants-2016_03
专利号
US09296741B2

反应笔记

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