Sodium Hydroxide → 1-methyl-1H-indazol-5-amine

HRID 563892

Reaktionsgleichung

Reaktionsgleichung von HRID 563892
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-])=O)=[CH:8][CH:9]=2)[CH:4]=[N:3]1.[OH-].[Na+]>Cl.[Fe]>[NH2:11][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:2]([CH3:1])[N:3]=[CH:4]2

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 2802111-Methyl-5-nitro-1H-indazole

Produkt 1

HCID 27680321-methyl-1H-indazol-5-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 313Hydrochloric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
72.5 °C

Versuchsvorschrift

To a stirred solution of 1-methyl-5-nitroindazole (3.24 g, commercially available) in concentrated hydrochloric acid (75 ml) was added iron powder (3.53 g) in portions over 10 minutes, allowing the reaction temperature to gradually rise to 52° C. On complete addition, the reaction mixture was heated to 70-75° C. for 1 hour, cooled to ambient temperature and stored for 18 hours. The mixture was chilled by the addition of ice then taken to pH 9 with aqueous sodium hydroxide filtered and the filtrate and insoluble solids extracted with ethyl acetate (three times). The extracts were combined, washed with brine and dried over magnesium sulphate then evaporated under reduced pressure to give 5-amino-1-methylindazole as a pale brown solid.

Aufarbeitung

  1. customto gradually rise to 52° C
  2. additionOn complete addition
  3. temperaturecooled to ambient temperature
  4. temperatureThe mixture was chilled by the addition of ice
  5. filtrationfiltered
  6. extractionthe filtrate and insoluble solids extracted with ethyl acetate (three times)
  7. washwashed with brine
  8. dry with materialdried over magnesium sulphate
  9. customthen evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8663474a09f148e8bb84a98e1ae501dd
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067592B2

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