Water → 3-Chloroisoquinolin-5-amine

HRID 1579132

반응식

HRID 1579132 반응식
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[C:9]([N+:12]([O-])=O)[CH:8]=[CH:7][CH:6]=2.O.[OH-].[Na+]>C(O)(=O)C.[Fe]>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[C:9]([NH2:12])[CH:8]=[CH:7][CH:6]=2

참가 물질

6

반응물 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 167480003-Chloro-5-nitroisoquinoline

생성물 1

HCID 167490403-Chloroisoquinolin-5-amine

시약·촉매·용매 2

HCID 23925Iron촉매2회HCID 176Acetic Acid용매

반응 조건

온도
60 °C

실험 절차

3-chloro-5-nitro-isoquinoline (20.9 g., 0.1170 mole, prepared according to the method of Example 1 hereinabove) was suspended in glacial acetic acid (160 ml), and water (160 ml) was then added while the temperature of the mixture was being raised to 60°C. Keeping the temperature between 60° and 70°C, powdered iron (15.2 g) was added slowly to the stirred mixture, and stirring was continued for 2 hours after addition of the iron was completed. The reaction mixture was allowed to stand overnight, and was then made alkaline with 20% w/v aqueous sodium hydroxide solution, and filtered. The residue was dried overnight, over silica gel in a vacuum oven at 50°C. The dried cake was then broken up and extracted -- three times with ether under reflux. The ether extract was boiled with charcoal, dried over anhydrous sodium sulphate, filtered, and the ether evaporated off to yield 9.25 g of 3-chloro-5-amino-isoquinoline of m.p. 176° - 177°C. Further ether extraction of the filter cake yielded another 4.2 g of 3-chloro-5-amino-isoquinoline of m.p. 175° - 177°C.

후처리

  1. custom, 0.1170 mole, prepared
  2. additionwas added slowly to the stirred mixture
  3. waitto stand overnight
  4. filtrationfiltered
  5. customThe residue was dried overnight, over silica gel in a vacuum oven at 50°C
  6. extractionextracted
  7. temperaturethree times with ether under reflux
  8. extractionThe ether extract
  9. dry with materialdried over anhydrous sodium sulphate
  10. filtrationfiltered
  11. customthe ether evaporated off

출처 및 근거

ORD 기록
ord-826de4240440431db9bca9ccfd428846
출처 데이터셋
uspto-grants-1976_01
특허 번호
US03930837

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