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聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯] → (+)-3-[6-(7-Chloroquinolin-2-ylmethoxy)chroman-3-ylmethyl]phenylamine

HRID 1684635
笔记
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反应方程式

HRID 1684635 反应方程式
[NH2:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][CH:6]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([OH:16])[CH:13]=2)[O:8][CH2:7]1.[H-].[Na+].Cl[CH2:23][C:24]1[CH:33]=[CH:32][C:31]2[C:26](=[CH:27][C:28]([Cl:34])=[CH:29][CH:30]=2)[N:25]=1.O>CN(C)C=O.C(OCC)(=O)C>[Cl:34][C:28]1[CH:27]=[C:26]2[C:31]([CH:32]=[CH:33][C:24]([CH2:23][O:16][C:12]3[CH:13]=[C:14]4[C:9](=[CH:10][CH:11]=3)[O:8][CH2:7][CH:6]([CH2:5][C:4]3[CH:3]=[C:2]([NH2:1])[CH:19]=[CH:18][CH:17]=3)[CH2:15]4)=[N:25]2)=[CH:30][CH:29]=1
参与物反应条件实验过程后处理来源与证据反应笔记

参与物

7

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 24758氢化钠HCID 10954844Quinoline, 7-chloro-2-(chloromethyl)-HCID 19039972(+)-3-(3-Aminobenzyl)chroman-6-ol

产物 1

HCID 19039973(+)-3-[6-(7-Chloroquinolin-2-ylmethoxy)chroman-3-ylmethyl]phenylamine收率 81%

试剂、催化剂与溶剂 2

HCID 6228
N,N-二甲基甲酰胺
溶剂
HCID 8857乙酸乙酯溶剂

反应条件

温度
0 °C

实验过程

To a stirred solution of 350 mg (1.37 mmole) of the product from Example 140 in 10 mL dimethylformamide at 0° C. was added 60 mg (1.51 mmole) sodium hydride. The mixture was stirred at 0° C. for 30 minutes, then 349 mg (1.64 mmole) 2-(chloromethyl)-7-chloroquinoline was added. The mixture was warmed to room temperature and stirred for 72 hours. The mixture was poured into water and extracted with ethyl acetate. The ethyl acetate extract was washed with water and brine, dried (MgSO4) and concentrated to give an oil. Flash chromatography on silica gel eluting with 40% ethyl acetate in hexanes yielded 476 mg (81%) of the title product as a solid, mp 128°-130° C. Analysis calculated for C26H23N2O2Cl: C, 72.47; H, 5.38; N, 650. Found: C, 72.47; H, 5.12; N, 6.43.

后处理

  1. temperatureThe mixture was warmed to room temperature
  2. stirringstirred for 72 hours
  3. extractionextracted with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. washwas washed with water and brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customto give an oil

来源与证据

ORD记录
ord-84635348c31b4f9ebd4573e0fe4059f1
来源数据集
uspto-grants-1997_06
DOI
10.6084/m9.figshare.5104873.v1
专利号
US05641789

反应笔记

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本页导航参与物反应条件实验过程后处理来源与证据反应笔记