Water → 3-Chloroisoquinolin-5-amine

HRID 1579132Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1579132
[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

Komponenten

6

Edukt 3

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

Produkt 1

HCID 167490403-Chloroisoquinolin-5-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysator2×HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-826de4240440431db9bca9ccfd428846
Quelldatensatz
uspto-grants-1976_01
Patentnummer
US03930837

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