Diethanolamine → 3-[N,N-bis(2-hydroxyethyl)amino]methyl-1,8-dihydroxy-9,10-anthraquinone

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Reaction Steps

A mixture of 3-bromomethyl-1,8-dihydroxy-9,10-anthraquinone (456 mg) and bis(2-hydroxyethyl)amine (600 mg) in N,N-dimethylformamide (20 mL) is stirred for 2 hours, and then partitioned between chloroform (100 mL) and water (100 mL). The organic layer is separated, washed with water (50 mL× 3), dried over sodium sulfate, and then concentrated to dryness. The residue is chromatographed on a silica gel column using chloroform-methanol (15:1 v/v) as the eluent. Upon concentration of the major fraction, 3-[N,N-bis(2-hydroxyethyl)amino] methyl-1,8-dihydroxy-9,10-anthraquinone is obtained as a solid: 1H NMR (CDCl3)δ: 2.77 (4H, t, NCH2CH2O), 3.78 (4H, t, NCH2CH2O), 4.78 (2H, s, CH2N=), 7.21-7.29 (5H, m, aromatic H), 11.95 (1H, s, OH), 12.00 (1H, s, OH).

Provenance & Evidence