Ammonium Chloride → 2-(3,3-dimethoxypropyl)-2H-indazole-6-ylamine

HRID 1825838Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1825838
[CH3:1][O:2][CH:3]([O:18][CH3:19])[CH2:4][CH2:5][N:6]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([N+:15]([O-])=O)[CH:11]=[CH:12]2)=[N:7]1.[NH4+].[Cl-]>CCO.O.[Fe]>[CH3:19][O:18][CH:3]([O:2][CH3:1])[CH2:4][CH2:5][N:6]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([NH2:15])[CH:11]=[CH:12]2)=[N:7]1

Komponenten

5

Edukt 2

HCID 25517Ammonium ChlorideHCID 220366272-(3,3-dimethoxypropyl)-6-nitro-2H-indazole

Produkt 1

HCID 221389282-(3,3-dimethoxypropyl)-2H-indazole-6-ylamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 19096565Water ethanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-(3,3-dimethoxypropyl)-6-nitro-2H-indazole (1.5 g, 5.66 mmol) and NH4Cl (254 mg, 4.53 mmol) in EtOH/H2O (2:1, 56 mL) at room temperature was added Fe (962 mg, 17.8 mmol) in a single poroom temperature ion and the resulting mixture was heated for 2 h at 70 C. The heating bath was removed and upon reaching room temperature the mixture was filtered through a pad of celite. The residue was washed with hot Methanol (5×20 mL) and the combined eluent was concentrated under reduced pressure. The residue was diluted with Ethyl acetate (30 mL) and filtered. Concentration of the organic layer under reduced pressure gave 2-(3,3-dimethoxypropyl)-2H-indazole-6-ylamine as an amber oil. 1H NMR (300 MHz, DMSO-D6) δ ppm 2.12 (m, 2 H), 3.24 (s, 6 H), 4.26 (m, 2 H), 4.32 (t, J=5.59 Hz, 1 H), 5.18 (m, 2 H), 6.52 (m, 2 H), 7.35 (d, J=8.48 Hz, 1 H) and 8.04 (s, 1 H).

Aufarbeitung

  1. temperaturethe resulting mixture was heated for 2 h at 70 C
  2. customThe heating bath was removed
  3. customupon reaching room temperature
  4. filtrationwas filtered through a pad of celite
  5. washThe residue was washed with hot Methanol (5×20 mL)
  6. concentrationthe combined eluent was concentrated under reduced pressure
  7. additionThe residue was diluted with Ethyl acetate (30 mL)
  8. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-78bbf95eb6ae4968bf6f58230ae25bb9
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07049307B2

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