Reacción #162983

Ecuación de reacción

Ethyl 3-(3-methyl-4-nitrophenyl)isoxazole-5-carboxylate

ammonium chloride

tetrahydrofuran

water

→

title compound

Rendimiento 81.0%

Ethyl 3-(4-amino-3-methylphenyl)isoxazole-5-carboxylate

Rendimiento 81.0%

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroReaction mixture
2. 2
   Temperaturawas cooled
3. 3
   Filtraciónfiltered through celite
4. 4
   OtroThe filtrate was evaporated to dryness under vacuum
5. 5
   workup.ADDITIONthe residue was diluted with EtOAc
6. 6
   LavadoThe organic layer was washed with water, brine
7. 7
   Secadodried over Na2SO4
8. 8
   Filtraciónfiltered
9. 9
   Concentraciónconcentrated in vacuo
10. 10
    OtroThe residue was purified by flash chromatography on silica gel
11. 11
    Lavadoeluting with 0-2% acetone in chloroform

Procedimiento

Ethyl 3-(3-methyl-4-nitrophenyl)isoxazole-5-carboxylate (1.0 equiv.), iron powder (2.0 equiv.), and ammonium chloride (3.0 equiv.) in a mixture of ethanol, tetrahydrofuran and water (4:2:1) were heated to 80° C. for 9 hours. Reaction mixture was cooled and filtered through celite. The filtrate was evaporated to dryness under vacuum and the residue was diluted with EtOAc. The organic layer was washed with water, brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel, eluting with 0-2% acetone in chloroform, to provide the title compound as a pale green solid (81%); 1H NMR (300 MHz, DMSO-d6) δ: 1.28-1.33 (t, J=7.2 Hz, 3H), 2.07 (s, 3H), 4.31-4.38 (q, 2H), 5.38 (s, 2H), 6.62-6.65 (d, J=8.4 Hz, 1H), 7.45-7.48 (dd, J=8.1 Hz, 1.8 Hz, 1H), 7.52 (s, 1H), 7.63 (s, 1H); IR (KBr) 3490, 3381, 3135, 2975, 2905, 1725, 1628, 1606, 1471, 1417, 1381, 1279, 1134, 1027, 924, 828, 769 cm−1.

Fuente