Ethanol → 1-((6-isopropylpyridin-2-yl)methyl)-3-methyl-1H-indazol-4-amine

HRID 706538Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 706538
[CH:1]([C:4]1[N:9]=[C:8]([CH2:10][N:11]2[C:19]3[C:14](=[C:15]([N+:20]([O-])=O)[CH:16]=[CH:17][CH:18]=3)[C:13]([CH3:23])=[N:12]2)[CH:7]=[CH:6][CH:5]=1)([CH3:3])[CH3:2].C(O)C.[Cl-].[NH4+]>O.[Fe]>[CH:1]([C:4]1[N:9]=[C:8]([CH2:10][N:11]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([NH2:20])[C:14]=3[C:13]([CH3:23])=[N:12]2)[CH:7]=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 679762021-((6-isopropylpyridin-2-yl)methyl)-3-methyl-4-nitro-1H-indazole

Produkt 1

HCID 679746421-((6-isopropylpyridin-2-yl)methyl)-3-methyl-1H-indazol-4-amineAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A flask equipped with an overhead stirrer and condenser was charged with 1-((6-isopropylpyridin-2-yl)methyl)-3-methyl-4-nitro-1H-indazole (25 g, 0.081 mol) and 150 mL of ethanol, followed by 45 g (0.805 mol) of iron powder. An equal amount of saturated ammonium chloride solution was added and the mixture was brought to 80° C. After 5 hours of heating, the mixture was allowed to cool to ambient temperature, diluted with water (500 mL) and filtered through GF/F filter paper multiple times to remove the iron and iron salts. The filtrate was extracted with EtOAc, dried over sodium sulfate and concentrated under reduced pressure. Column chromatography (1:1 ethyl acetate/hexane to 100% ethyl acetate) afforded 12.6 g (56%) of 1-((6-isopropylpyridin-2-yl)methyl)-3-methyl-1H-indazol-4-amine.

Aufarbeitung

  1. customA flask equipped with an overhead stirrer and condenser
  2. customwas brought to 80° C
  3. temperatureAfter 5 hours of heating
  4. filtrationfiltered through GF/F
  5. filtrationfilter paper multiple times
  6. customto remove the iron and iron salts
  7. extractionThe filtrate was extracted with EtOAc
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f4cbe4d030be44a0959f28bc7568a39f
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09174981B2

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