Reaktion #961066

Reaktionsgleichung

NaOH

SnCl2.2H2O

HCl

3,7-dimethyl-5-nitrobenzo[d]isoxazole

→

title product

Ausbeute 59.0%

3,7-dimethylbenzo[d]isoxazol-5-amine

Ausbeute 59.0%

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with EtOAc
2. 2
   TrocknenThe combined organic layers were dried over MgSO4
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated under reduced pressure
5. 5
   SonstigeThe crude product was purified by silica gel column chromatography (hexane/EtOAc 0-55%)

Vorschrift

To a suspension of 3,7-dimethyl-5-nitrobenzo[d]isoxazole (Step 46.5) (50 mg, 0.260 mmol) in acetic acid (1.5 mL) was added dropwise a solution of SnCl2.2H2O (176 mg, 0.781 mmol) in HCl conc (0.316 mL, 10.41 mmol) and the resulting mixture was stirred at RT overnight. The reaction was poured into a cold 4N NaOH solution and extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (hexane/EtOAc 0-55%) to afford the title product (25 mg, 0.153 mmol, 59% yield) as beige solid. tR: 0.57 min (LC-MS 2); ESI-MS: 163 [M+H]+; Rf=0.23 (hexane/EtOAc 1:1).

Quelle