O-Phenylenediamine → HCID 17863286, compound

Participants

Reaction Conditions

Reaction Steps

The title compound was synthesized according to a modified literature procedure.30 Hexaketocyclohexane octahydrate (10.0 g, 32.0 mmol) and 1,2-phenylenediamine SM17 (10.4 g, 96.0 mmol) were refluxed in 500 ml of glacial acetic acid:ethanol (1:1) at 140° C. for 24 hours. The reaction mixture was then filtered and washed with ca. 200 ml of hot glacial acid. The solid was then refluxed with 200 ml of 30% nitric acid for 3 hours at 140° C. The yellow solid (12.6 g) was filtered and dried under vacuum. An amount 2.0 g was sublimed at high vacuum (3.2×10−6 torr and t=350° C.) to yield 0.77 g (estimated extrapolated yield=40%) of yellow solid. The yield could be increased with prolonged sublimation time. This compound is slightly soluble in CHCl3. 1H NMR (CDCl3, 300 MHz) δ 8.73-8.69 (dd, J=6.6 Hz; J2=3.6 Hz, 6H), 8.08-8.043 (m, 6H). 13C NMR (CDCl3, 75 MHz), 143.57, 132.30, 130.65, 119.05, 98.58. Anal. Calcd. for C24H12N6: C, 74.99; H, 3.15; N, 21.86. Found: C, 74.76; H, 3.11; N, 21.66.

Provenance & Evidence