Ammonium Chloride → 5-(2-Chloropyridin-4-yloxy)pyridin-2-amine

HRID 450446

Reaktionsgleichung

Reaktionsgleichung von HRID 450446
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[N:11][C:12]([N+:15]([O-])=O)=[CH:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1.[Cl-].[NH4+]>C1COCC1.CO.[Zn]>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[N:11][CH:10]=2)[CH:5]=[CH:4][N:3]=1

Komponenten

6

Edukt 2

HCID 25517Ammonium ChlorideHCID 593227792-Chloro-4-((6-nitropyridin-3-yl)oxy)pyridine

Produkt 1

HCID 593227885-(2-Chloropyridin-4-yloxy)pyridin-2-amineAusbeute 103 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2-Chloro-4-(6-nitropyridin-3-yloxy)pyridine (0.540 g, 2.146 mmol) was dissolved in THF (54 ml) and MeOH (54 ml). Ammonium chloride (1.148 g, 21.46 mmol) was then added, followed by zinc dust (1.403 g, 21.46 mmol). The reaction was stirred at RT for 45 minutes, filtered over Celite® and concentrated under reduced pressure to yield 5-(2-chloropyridin-4-yloxy)pyridin-2-amine as a brown solid (0.49 g, 99%). It was used as is in the next reaction. 1H NMR (400 MHz, DMSO-d6): δ 8.46 (d, 1H), 7.81 (d, 1H), 7.30 (dd, 1H), 6.90 (m, 2H), 6.50 (d, 1H), 6.08 (s, 2H); MS (ESI) m/z: 222.0 (M+H+).

Aufarbeitung

  1. filtrationfiltered over Celite®
  2. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-23496e601f664a58b0ac285982168897
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486951B2

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