Reaktion #956179

Reaktionsgleichung

Sodium hydroxide

hydrochloric acid

5-azido-1,6-naphthyridine

→

crude product

Ausbeute 69.2%

1,6-Naphthyridin-5-amine

Ausbeute 69.2%

Lösungsmittel

EtOAc

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA yellow precipitate formed
2. 2
   FiltrationThe mixture was filtered
3. 3
   Sonstigeto give a yellow solid
4. 4
   SonstigeA white precipitate formed
5. 5
   FiltrationThe mixture was filtered
6. 6
   Extraktionthe filtrate was extracted with EtOAc (200 mL×6)
7. 7
   TrocknenThe organic phase was dried over sodium sulfate
8. 8
   Einengenconcentrated under reduced pressure

Vorschrift

To a suspension of 5-azido-1,6-naphthyridine (3.4 g, 19.9 mmol) in methanol (40 mL) was added hydrochloric acid (30 mL). Stannous chloride dihydrate (22.5 g, 99.5 mmol) was added. The mixture was stirred at 75° C. for 3.5 h. A yellow precipitate formed. The mixture was filtered to give a yellow solid. The solid was suspended in EtOAc (200 mL). Sodium hydroxide (saturated aqueous solution) was added to adjust pH to 9. A white precipitate formed. The mixture was filtered and the filtrate was extracted with EtOAc (200 mL×6). The organic phase was dried over sodium sulfate and concentrated under reduced pressure to give 2.0 g of the crude product as a yellow solid. MS (ESI): m/z 146 [M+H]+.

Quelle