Reaktion #60110

Reaktionsgleichung

sodium hydride

acetic anhydride

2-amino-3-nitro-6-chloropyridine

→

product

Ausbeute 8.2%

N-(6-chloro-3-nitro-2-pyridyl)acetamide

Ausbeute 8.2%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred at room temperature overnight
2. 2
   SonstigeThe reaction mixture was quenched with water
3. 3
   Einengenconcentrated under reduced pressure
4. 4
   workup.DISSOLUTIONThe crude product was dissolved in dichloromethane
5. 5
   Waschenwashed with brine
6. 6
   TrocknenThe organic layer was dried with sodium sulfate
7. 7
   Einengenconcentrated under vacuo
8. 8
   SonstigeThe crude was purified by flash chromatography
9. 9
   Wascheneluting 78% hexane

Vorschrift

To a suspension of sodium hydride (120 mg, 5 mmole) in tetrahydrofuran(10 ml), a solution of 2-amino-3-nitro-6-chloropyridine (870 mg, 5 mmole) in 20 ml of tetrahydrofuran (20 ml) was added. The reaction mixture was stirred at room temperature for 30 min. A solution of acetic anhydride (377 μl, 6 mmole) in tetrahydrofuran (10 ml) was added and stirred at room temperature overnight. The reaction mixture was quenched with water and concentrated under reduced pressure. The crude product was dissolved in dichloromethane and washed with brine. The organic layer was dried with sodium sulfate and then concentrated under vacuo. The crude was purified by flash chromatography, eluting 78% hexane: 22% ethyl acetate to give a yellow product (88 mg).

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