Hexane → 4-(2,3-Dihydrothieno[3,4-b][1,4]dioxin-5-yl)aniline

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Reaction Steps

A solution of 1-(3,4-ethylenedioxythien-2-yl)-4-nitrobenzene (0.663 g, 2.52 mmol) in 95% ethanol (60 mL) containing platinum on sulfide carbon (50 mg) was added hydrazine hydrate (1.0 mL). The mixture was refluxed for 10 hours. After cooling, the mixture was filtered and the solvent was evaporated to give a solid. Addition of hexane followed by filtration gave 1-(3,4-ethylenedioxythien-2-yl)-4-aminobenzene. It was recrystallized from ethanol, 0.39 g, yield=66%, mp=98.5-99° C. IR (KBr; cm-1) 3433, 3352, 3032, 2924, 1624, 1520, 1428, 1365, 1288, 1170, 1071, 920 and 833. 1H NMR(CDCl3 ; δ in ppm): 3.604 (br, s, 2H), 4.208 (m, 4H), 6.176 (s, 1H), 6.651 (d, J=9.6 Hz, 2H) and 7.492 (d, J=9.6 Hz, 2H). 13C NMR(CDCl3 ; δ in ppm): 64.45, 64.59, 95.61, 115.10, 117.98, 123.60, 127.25, 136.61, 142.09 and 145.20. MS(EI) m/z (rel int): 233 [(M)+, 55%], 177 [(M+ --C3H4O), 6.6%], 149 [(M+ --C4H4O2, 11%] and 136 [(M+ --C5H5O2) 100%]. Anal. Calcd for C12H11NO2S: C, 61.78; H, 4.75; N, 6.00; S, 13.74. Found: C, 60.82; H. 4.87; N, 5.64; S, 12.86.

Provenance & Evidence