Week of 10/9 to 10/12
Monday, 10/9
Bromination of 1,8-naphthotriazine to form 8-bromonaphthalen-1-amine. Reaction was stirred, signifigant dark foamy sludge formed at 80 C.
Tuesday, 10/10
Second attempt to nitrate 8-bromonaphthalen-1-amine under alternative nitration conditions, since m-CPBA failed to react. 1.2g sodium nitrite was mixed with concentrated sulphuric acid and the 8-bromonaphthalen-1-amine was added. The reaction was then quenched in an 1:1 mixture by weight of copper (I) sulphite and sodium nitrite. The resulting mix was filtered, extracted with methylene chloride and rotavaped, with <1% yield by weight (~5g -> 50mg). The proton NMR shows evidence of the amine being oxidized.
Wednesday 10/11
Ran proton NMR of
7,8-ortho-methylpiperidine-1-naphthanitrile. Proton tells us that the product had not been purified through the column. Sublimation was attempted at some point, but there was no change in the purity of the final product.
Thursday 10/12 small scale acid wash of 7,8-ortho-methylpiperidine-1-naphthanitrile with 1M HCl. TLC indicates cleaner product when compared to precursor sample. Proton NMR needed to confirm, but due to a power outage, the NMR is not operational.
I started a large batch bromination of the 1,8-naphthotriazine to form [8-bromonaphthalen-1-amine] at a 2x scale when compared to the one I did on monday.
Afterword: Fall break happened, and the bromination went poorly. I had wanted to come in Friday the 13th but ended up staying inside the whole day. The bromination was stirring at room temperature for well over 72 hours and was overcooked everything became tar. The NMR essentially shat the bed due to the power outage. The NMR could not be auto shimmed on the Z-axis, and the carbon-13 NMR stopped working. Then the proton NMR degraded to the point of being unusable and died some time the next week (week of 10/16-10/20). This was supposed to be published the 15th, but is written on the 24th.