Glycerol → 2,3-Dihydro[1,4]dioxino[2,3-h]quinoline

Participants

Reaction Conditions

Reaction Steps

A mixture of concentrated sulphuric acid (30 ml), boric acid (2.29 g; 47.20 mmol) iron (II) sulphate heptahydrate (1.09 g; 3.93 mmol) and 3-nitrobenzene sulphonic acid sodium salt (9.5 g; 42.36 mmol) was cooled to 0° C. before addition of glycerol (11 ml; 151.31 mmol) and 2,3-dihydro-1,4-benzodioxin-5-amine (4.6 g; 30.26 mmol) followed by water (30 ml). The mixture was then heated to 140° C. and stirred for 4 hours. The reaction was then cooled to rt before being poured onto ice water (150 ml) and filtered. The resulting mixture was then basified to pH 8 with 6N NaOH and stirred with EtOAc for 30 mins. The organics were separated and the aqueous layer extracted with EtOAc×3. The combined organic layers were filtered through kieselguhr, washed with brine and dried with MgSO4. The solvents were removed to afford the desired product (3.65 g; 65%).

Provenance & Evidence