Ammonium Chloride → 3-chloro-1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-5-ylamine

HRID 1790164Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1790164
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-])=O)[CH:9]=2)[N:4]([CH2:14][CH2:15][N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[N:3]=1.[Cl-].[NH4+]>C(O)C.[Fe]>[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH2:11])[CH:9]=2)[N:4]([CH2:14][CH2:15][N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[N:3]=1

Komponenten

5

Edukt 2

HCID 25517Ammonium ChlorideHCID 220365953-chloro-5-nitro-1-(2-pyrrolidin-1-yl-ethyl)-1H-indazole

Produkt 1

HCID 696527543-chloro-1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-5-ylamineAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 3-Chloro-5-nitro-1-(2-pyrrolidin-1-yl-ethyl)-1H-indazole (0.40 g, 1.4 mmol), iron powder (0.76 g, 14 mmol), and ammonium chloride (37 mg, 0.68 mmol) in 80% ethanol was heated to reflux for 3 hours, cooled to room temperature and concentrated under reduced pressure. The residue was stirred in triethylamine/ethyl acetate (1/4, 20 mL) for 15 minutes, filtered through a plug of silica gel, which was rinsed with triethylamine/ethyl acetate (1/4). The filtrate was concentrated under reduced pressure to provide the title compound (0.30 g, 84%). 1H NMR (300 MHz, DMSO-d6) ppm 1.62 (m, 4H), 2.44 (m, 4H), 2.81 (t, J=6.44, 2H), 4.34 (t, J=6.44, 2H), 5.05 (s, 2H), 6.58 (m, 1H), 6.88 (m, 1H), 7.12 (m, 1H); MS (DCI/NH3) m/z 265 [M+H]+.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. concentrationconcentrated under reduced pressure
  4. filtrationfiltered through a plug of silica gel, which
  5. washwas rinsed with triethylamine/ethyl acetate (1/4)
  6. concentrationThe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c1aafaf9b8134916a2f3fa6a6260862d
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07071182B2

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