聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯] → HCID 11701688，化合物

HRID 260068

反应方程式

HRID 260068 反应方程式
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[K+].[K+].ClCC(N[C:17]1[CH:26]=[C:25]([NH:27][C:28](=[O:31])[CH2:29][Cl:30])[C:24]([OH:32])=[C:23]2[C:18]=1[CH:19]=[CH:20][C:21]([CH3:33])=[N:22]2)=O.[OH2:34]>C(O)(=O)C>[Cl:30][CH2:29][C:28]([NH:27][C:25]1[C:24](=[O:32])[C:23]2[N:22]=[C:21]([CH3:33])[CH:20]=[CH:19][C:18]=2[C:17](=[O:34])[CH:26]=1)=[O:31]

参与物

5

反应物 3

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]HCID 24502重铬酸钾2 次HCID 115374375,7-Bis(chloroacetamido)-8-hydroxy-2-methylquinoline

产物 1

HCID 11701688HCID 11701688，化合物收率 59%

试剂、催化剂与溶剂 1

HCID 176醋酸溶剂2 次

实验过程

This compound was prepared by the oxidation of the corresponding acylamido with potassium dichromate in glacial acetic acid. In a 500 ml. round-bottom flask equipped with a magnetic bar, 5,7-bis (chloroacetamido)-8-hydroxy-2-methylquinoline (32) (prepared as described in Example 32) (3.42 g., 0.01 mol) was suspended in 122 ml. of glacial acetic acid. A solution of potassium dichromate (8.8 g., 0.03 mol) in 115 ml. of water was added and the resulting dark solution was stirred at room temperature overnight. The solution was extracted with dichloromethane (12×50 ml. ). The organic extracts were washed with 3% sodium bicarbonate solution (200 ml. ), dried with magnesium sulfate, and rotoevaporated to yield a bright yellow solid. After vacuum drying, the nearly pure product weighed 1.56 g. (yield of 59%). The product was recrystallized from ethyl acetate: mp 196°-200° C. (dec.); 1H NMR (CDCl3) δ2.76 (3H, s, C-2CH3), 4.23 (2H, s, C-7NHCOCH2Cl), 7.56 (1H, d, J=8.1 Hz, C-3H), 7.89 (1H, s, C-6H), 8.30 (1H, d, J=8.1 Hz, C-4H), 9.48 (1H, br. s, C-7NH); IR (KBr) vmax 3299, 3078, 2948, 1712, 1683, 1641, 1614, 1588, 1515, 1398, 1384, 1323, 1130 cm-1 ; EIMS, m/e (relative intensity) 264/266 (M+, 2.9/1, 67) 229 (62), 215 (74), 201 (43), 188 (86), 161 (base), 132 (21); HRMS, m/e for C14H9ClN2O3, calculated 64.030170, found 264.029824; analysis for C14H9ClN2O3 calculated: C, 54.46; H, 3.43; Cl, 13.40; N, 10.58; found: C, 54.19; H, 3.37; Cl, 13.29; N, 10.36.

后处理

  1. customround-bottom flask equipped with a magnetic bar
  2. extractionThe solution was extracted with dichloromethane (12×50 ml. )
  3. washThe organic extracts were washed with 3% sodium bicarbonate solution (200 ml. )
  4. dry with materialdried with magnesium sulfate
  5. customto yield a bright yellow solid
  6. customAfter vacuum drying
  7. customThe product was recrystallized from ethyl acetate

来源与证据

ORD记录
ord-b5a9477980f648f597786af0129f937f
来源数据集
uspto-grants-1996_06
专利号
US05525611

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