Reaktion #614779

Reaktionsgleichung

ammonium chloride

hydroxyl-amine

2-[(1a-methyl-1,1a,2,7b-tetrahydrocyclopropa[c]chromen-7-yl)oxy]-5-nitropyridine

Intermediate 126

2-[(1a-methyl-1,1a,2,7b-tetrahydrocyclopropa[c]chromen-7-yl)oxy]-5-nitropyridine

water

ammonium chloride

→

title compound

Ausbeute 66.7%

6-[(1a-methyl-1,1a,2,7b-tetrahydrocyclopropa[c]chromen-7-yl)oxy]-3-pyridinamine

Ausbeute 66.7%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITthe reaction was left
2. 2
   workup.STIRRINGstirring for an other 5 hours
3. 3
   FiltrationThe iron was then filtered off over a pad of celite
4. 4
   workup.ADDITIONthe solution was diluted with an aqueous saturated solution of NaHCO3 (100 ml) and ethyl acetate (200 ml)
5. 5
   SonstigeTwo phases were separated
6. 6
   Extraktionthe aqueous layer was extracted with ethyl acetate
7. 7
   Trocknendried over sodium sulphate
8. 8
   Filtrationfiltered
9. 9
   Sonstigeevaporated
10. 10
    SonstigeThe residue was purified by silica gel chromatography (Companion system

Vorschrift

To a solution of 2-[(1a-methyl-1,1a,2,7b-tetrahydrocyclopropa[c]chromen-7-yl)oxy]-5-nitropyridine (Intermediate 126, 250 mg) in tetrahydrofuran (6 ml)/water (3 ml) were added iron (234 mg, 4.19 mmol) and ammonium chloride (224 mg, 4.19 mmol). The reaction mixture was stirred at room temperature overnight at which time UPLC showed partial formation of the target compound with some hydroxyl-amine intermediate, therefore additional 3 equivalents of ammonium chloride and iron were added and the reaction was left stirring for an other 5 hours. The iron was then filtered off over a pad of celite and the solution was diluted with an aqueous saturated solution of NaHCO3 (100 ml) and ethyl acetate (200 ml). Two phases were separated and the aqueous layer was extracted with ethyl acetate. Organic layers were combined, dried over sodium sulphate, filtered and evaporated. The residue was purified by silica gel chromatography (Companion system, with a gradient from cyclohexane/ethyl acetate 8:2 to cyclohexane/ethyl acetate 1:1) to give the title compound as a light brown solid (150 mg).

Quelle