苯酚 → 4-(O-Benzylhydroxylamino)-3-methoxy-2-methylpyridine

HRID 1000

反应方程式

HRID 1000 反应方程式
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[C:3]=1[O:9][CH3:10].C1(O)C=CC=CC=1.[CH2:18]([O:25][NH2:26])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[OH-].[Na+]>C(Cl)Cl>[CH2:18]([O:25][NH:26][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[C:3]=1[O:9][CH3:10])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

参与物

6

反应物 4

HCID 996苯酚HCID 14798二甲基对苯二胺二盐酸HCID 102313邻苄基羟胺HCID 105830464-氯-3-甲氧基-2-甲基吡啶

产物 1

HCID 152793584-(O-Benzylhydroxylamino)-3-methoxy-2-methylpyridine

试剂、催化剂与溶剂 1

HCID 6344二氯甲烷溶剂

实验过程

16 g of 4-chloro-3-methoxy-2-methylpyridine, 63 g of phenol and 40 g of O-benzylhydroxylamine are stirred at 120° C. under nitrogen for 4 hours. After cooling, the mixture is shaken with 500 ml of 2N NaOH and CH2Cl2. The aqueous phase is extracted a second time with CH2Cl2. After concentrating the combined CH2Cl2 phases, excess O-benzylhydroxylamine is distilled off in vacuo at 0.6 mm. The residue crystallizes on stirring with hexane. After filtering off with suction and washing with hexane 21.6 g=88.4% of product remain. The product is recrystallized from ethyl acetate. M.p.: 130° C.

后处理

  1. temperatureAfter cooling
  2. extractionThe aqueous phase is extracted a second time with CH2Cl2
  3. concentrationAfter concentrating the combined CH2Cl2 phases, excess O-benzylhydroxylamine
  4. distillationis distilled off in vacuo at 0.6 mm
  5. customThe residue crystallizes
  6. filtrationAfter filtering off with suction
  7. washwashing with hexane 21.6 g=88.4% of product
  8. customThe product is recrystallized from ethyl acetate

来源与证据

ORD记录
ord-5d39e4809233431997c0a9624f5079c5
来源数据集
uspto-grants-1998_03
专利号
US05723450

关联笔记

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