Formamide → Anthracene-9,10-diamine

Participants

Reaction Steps

20 g of anthraquinone was heated at boiling point with 200 ml formamide for 4 hours. The supernatent anthraquinone slowly disappeared while yellow crystals deposited. The solution was cooled, suction filtered and washed thoroughly with alcohol. The resultant 9,10-diformylaminoanthracene was recrystalized from formamide giving long yellow crystals mpt 439° C. Chemical analysis for C16 H12 O2 N2 was calculated N 10.60%, found N10.88%. 40 g of KOH was dissolved in 100 ml of methanol and 10 g of the 9,10 diformylaminoanthracene prepared above was added and formed a deep red brown solution. This was heated at boiling point for one hour, when red glistening crystals separated. The solution was cooled, suction filtered with the exclusion of air and the crystals washed with methanol. The crystal mass was dissolved in acetone, filtered as necessary and the filtrate carefully mixed with petroleum ether to deposit 9,10 diaminoanthracene as glistening flakes. Recrystalization from acetone gave deep red crystals. Chemical analysis for C14 H12 N2 was calculated C 80.75%, H 5.81%, N 13.44% found C 81.06%, H 5.18%, N 12.47%.

Provenance & Evidence