海萝胶 → 2-(2-Amino-8-hydroxy-6-sulfo-1-naphthylazo)-5-nitrobenzoic acid

HRID 2071891

反应方程式

HRID 2071891 反应方程式
[N+:1]([C:4]1[CH:12]=[C:8]([C:9]([OH:11])=[O:10])[C:7]([NH2:13])=[CH:6][CH:5]=1)([O-:3])=[O:2].[N:14]([O-])=O.[Na+].Cl.[Na].[CH:20]1[C:29]2[C:24](=[C:25]([OH:34])[CH:26]=[C:27]([S:30]([OH:33])(=[O:32])=[O:31])[CH:28]=2)[CH:23]=[C:22]([NH2:35])[CH:21]=1.O.O.O.C([O-])(=O)C.[Na+]>O.[OH-].[Na+].C(O)(=O)C>[NH2:35][C:22]1[CH:21]=[CH:20][C:29]2[C:24](=[C:25]([OH:34])[CH:26]=[C:27]([S:30]([OH:33])(=[O:32])=[O:31])[CH:28]=2)[C:23]=1[N:14]=[N:13][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][C:8]=1[C:9]([OH:11])=[O:10]

参与物

10

反应物 6

HCID 313海萝胶HCID 70222-氨基-8-萘酚-6-磺酸2 次HCID 120322-氨基-5-硝基苯甲酸HCID 5360545钠HCID 23665404三水合醋酸钠HCID 23668193亚硝酸钠

产物 1

HCID 1358507132-(2-Amino-8-hydroxy-6-sulfo-1-naphthylazo)-5-nitrobenzoic acid

试剂、催化剂与溶剂 3

HCID 176醋酸溶剂HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂4 次HCID 14798二甲基对苯二胺二盐酸溶剂2 次

反应条件

温度
90 °C

实验过程

To a filtered solution of 18.2 g of 5-nitroanthranilic acid in 300 ml of water and 22 ml of 5N sodium hydroxide is added 6.9 g of sodium nitrite. The resulting, slightly warm solution is poured over a rapidly stirred mixture of 34.0 ml of concentrated hydrochloric acid, 50 ml of acetic acid, 350 g of ice and 100 ml of water in a 2 liter beaker. This mixture is stirred in an ice bath during preparation of a solution of the sodium salt of 7-amino-1-naphthol-3-sulfonic acid (gamma acid). Thus, to a solution of 28 g of 85% pure 7-amino-1-naphthol-3-sulfonic acid in 50 ml of water and 24 ml of 5N sodium hydroxide is added 30 g of sodium acetate trihydrate in 30 ml of water. The resulting solution is added to the rapidly stirred diazonium salt solution and the mixture is stirred for approximately 5 minutes then is heated to 90° C. and allowed to stand overnight at room temperature. The mixture is filtered and the product is washed with a small amount of water. The product if then dissolved in 1300 ml of hot water and filtered through a steam heated, sintered funnel. To the filtrate maintained at 80° C. is added 140 g of sodium formate. The mixture is cooled to room temperature and is filtered. The product is washed with a 10% aqueous solution of sodium formate followed by ethanol to give 2-(2-amino-8-hydroxy-6-sulfo-1-naphthylazo)-5-nitrobenzoic acid, 6'-sodium salt.

后处理

  1. waitto stand overnight at room temperature
  2. filtrationThe mixture is filtered
  3. washthe product is washed with a small amount of water
  4. dissolutionThe product if then dissolved in 1300 ml of hot water
  5. filtrationfiltered through a steam
  6. temperatureheated
  7. temperatureTo the filtrate maintained at 80° C.
  8. additionis added 140 g of sodium formate
  9. temperatureThe mixture is cooled to room temperature
  10. filtrationis filtered
  11. washThe product is washed with a 10% aqueous solution of sodium formate

来源与证据

ORD记录
ord-c2a76349b1bc40f58b9a75c2d9161b3b
来源数据集
uspto-grants-1977_09
专利号
US04049640

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