反应详情

5-aminoacenaphthene (7.0 g, 41.4 mmol) was dissolved in a mixture of ether (100 mL) and ethyl acetate (25 mL). To this solution was added 5.2 mL of a 5 M solution of cyanogen bromide in acetonitrile (25.6 mmol of cyanogen bromide). The solution was stirred overnight, with the gradual appearance of gray precipitate. The solid was removed by filtration (the hydrobromide of 5-aminoacenaphthene) and the resulting filtrate concentrated in vacuo to afford a semi-solid residue. Ether (60 mL) was added to the residue and the mixture was stirred overnight. The solid was removed (more hydrobromide of 5-aminoacenaphthene) and the filtrate concentrate to approximately 20 mL and then diluted with warm cyclohexane (15 mL). Upon standing at room temperature, off-white crystals were deposited. They were collected, washed with cyclohexane-ether (1:1) and dried in vacuo to give 1.5 g of pure product, mp: 163-65° C.

1. customThe solid was removed by filtration (the hydrobromide of 5-aminoacenaphthene) and the resulting filtrate
2. concentrationconcentrated in vacuo
3. customto afford a semi-solid residue
4. stirringthe mixture was stirred overnight
5. customThe solid was removed (more hydrobromide of 5-aminoacenaphthene) and the filtrate
6. concentrationconcentrate to approximately 20 mL
7. additiondiluted with warm cyclohexane (15 mL)
8. customUpon standing at room temperature
9. customThey were collected
10. washwashed with cyclohexane-ether (1:1)
11. customdried in vacuo