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

HRID 450461Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 450461
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[N:11][C:12]([N+:16]([O-])=O)=[CH:13][C:14]=2[CH3:15])[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[C:14]([CH3:15])=[CH:13][C:12]([NH2:16])=[N:11][CH:10]=2)[CH:5]=[CH:4][N:3]=1

Komponenten

6

Edukt 2

HCID 25517Ammonium ChlorideHCID 866416892-Chloro-4-(4-methyl-6-nitropyridin-3-yloxy)pyridine

Produkt 1

HCID 866416905-(2-Chloropyridin-4-yloxy)-4-methylpyridin-2-amineAusbeute 103 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2-Chloro-4-(4-methyl-6-nitropyridin-3-yloxy)pyridine was dissolved in THF (11.95 ml)/methanol (11.95 ml) and ammonium chloride (0.256 g, 4.78 mmol) was added, followed by zinc dust (0.313 g, 4.78 mmol). The mixture stirred at RT for 1.5 hours before it was filtered through Celite®. The filtrate was evaporated under reduced pressure to yield a magenta film which was partitioned between ethyl acetate/THF (4:1) and water. The organic layer was washed with brine, dried (MgSO4) and evaporated to yield 5-(2-chloropyridin-4-yloxy)-4-methylpyridin-2-amine as a brown oil (0.116 g, 103%), which was used in the next step without purification. MS (ESI) m/z: 236.1 (M+H+).

Aufarbeitung

  1. additionwas added
  2. filtrationwas filtered through Celite®
  3. customThe filtrate was evaporated under reduced pressure
  4. customto yield a magenta film which
  5. customwas partitioned between ethyl acetate/THF (4:1) and water
  6. washThe organic layer was washed with brine
  7. dry with materialdried (MgSO4)
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-32e32b7350164619aebc8d889eddd788
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486951B2

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