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16.17.3.3.3 Method 3: By Nitration

DOI: 10.1055/sos-SD-016-01192

Seela, F.; Ramzaeva, N.; Rosemeyer, H.Science of Synthesis, (2004161010.

Nitration of purines gives 8-nitropurines; 8-nitrotheophylline and 8-nitrotheobromine are obtained with nitrous acid.[‌348‌,‌349‌] Caffeine,[‌350‌] 3-methylxanthine, and 9-methylxanthine[‌351‌] can also be converted directly with nitric acid into their 8-nitro derivatives, though in most cases yields and physical data have not been reported. Thus, 9-methylxanthine is converted into 9-methyl-8-nitroxanthine on heating in 50% nitric acid.[‌351‌]

8-Meeeeeeeeeeeeee eee eeeeeee eeeeeeeee eeeee eeee eeee eeeeeeeeee (MeMM8, M8M, ee, 88e) ee eeee 8-eeeeeeeeeeeee ee 88% eeeee.[‌888‌] Meee eeee ee eee eeeeeeeee eeeeeeee eee eeeeeeeee eeeeeee ee eee eeeeeeeee eee, MM8+. Mee eeee eeee eeeeeeeee eeeee (e.e., MM8+MM8) eeeeeee eeeeeeee eeeeeeeee eeeeeeeee eeee eee eeee ee eeeeeeee ee e eeeeeeeee eee. Me eeeee ee eeeeeee eeeeeeeee ee eee eeee eeeeeeeee M-eeeeeeeeeee eeeeeeee eeeeeeeeeee, eeeeeeeee eeeeeeeeeeeeeeeee ee eeee ee eeeeeee eeeeeeee ee eeeeeeee eeeeeeeeeeee; e.e. eeeeeeeee ee 8-eeeeee-8-eeeeeeeeeeeeee ee eeee eee 8-eeeee eeeeeee 888 (M8=M; M8=Me; M8=Me) (Meeeee 88).[‌888‌] Meeeeeeee, 8-eeeeee-, 8,8-eeeeeeee-, eee 8,8,8-eeeeeeeeeeeeeeeee eeee eee eeeeeeeeeeeee 8-eeeee eeeeeeeeeee ee 8888% eeeee.[‌888‌]

Meeeee 88 8-Meeeeeeeeeeeee ee Meeeeeeee ee Meeeeeee Meeeeeeeeee[‌888‌]

Meeeeeeeeee 88

M8 M8 M8 Meeeeeeeee Meeee (%) Mee
Me M M 88% MMM8, MeMM, 888°M, 88eee 88 [‌888‌]
M Me M 88% MMM8, MeMM, 888°M, 88eee 88 [‌888‌]
M Me M 88% MMM8, MeMM, 888°M, 88eee 88 [‌888‌]
M M Me MM8+MM8, MeMM, 888°M, 8e 88 [‌888‌]
Me Me M 88% MMM8, Me8M, 88°M, 8e 88 [‌888‌]
Me Me M 88% MMM8, MeMM, eeeeee, 88eee 88 [‌888‌]
Me M Me MM8+MM8, eeeeeeeee, 888°M, 8.8e 88 [‌888‌]
M Me Me MM8+MM8, MeMM, 888°M, 8e 88 [‌888‌]
M Me Me MM8+MM8, MeMM, 888°M, 8e 88 [‌888‌]
Me Me Me MM8+MM8, MeMM, 88°M, 8e 88 [‌888‌]
Me Me Me MM8+MM8, MeMM, 888°M, 8.8e 88 [‌888‌]
M M M 888% MMM8, MeMM, eeeeee, 8e 88 [‌888‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeeeeeeeeee (888, M8=M8=M8=M); Meeeeee Meeeeeeee:[‌888‌]

Meeeeeee (8.88e, 88.8eeee) eee eeeeee ee eeeeeee MeMM (88eM) ee 888°M ee ee eee eeee, eee eeee 888% MMM8 (8eM, 88.8eeee) eee eeeee eeeeeeee eeee eeeeeeee. Mee eeeeeeeeee eee eeeeeeee eee 8e. Meeee eeeeeee, eee eeeeeeeeeee eee eeeeeeeee, eeeeee, eee eeeee ee 888°M. Mee eeeee eee eeeeeeeeeeeeee (8.8M MMe, 888eM) ee eeee e eeeeeeeee eeeeeeeeeee eeeeee; eeeee: 8.88e (88%); ee >888°M.

8-Meeeee-8-eeeeee-8-eeeeeeeeeeeee (888, M8=M; M8=Me; M8=Me); Meeeeee Meeeeeeee:[‌888‌]

Me e eeee ee eeeeeeeee eeeeeeeeeeeeeeeee (888ee, 8eeee) ee eeeeeee MeMM (88eM) eee eeeee 8-eeeeee-8-eeeeeeeeeeeeee (888ee, 8eeee) eeee eeeeeeee. Mee eeeeeee eee eeeeee ee 888°M eee 8e eeeee eeeeeeeee eeeeeeeeee eee eee eeee eeeeeeeeee ee eeeeeee ee eeeee. Mee eeeeeee eee eeeeeee eeee eee (88e) eeee eeeeeeee eee 88eee. Mee eeeeeeeeeee eee eeeeeeeee eee eeee, eeeee eeeeeeeeeeeeeeeee (8.8M MMe, 88eM), eeeeee eeeeeeee; eeeee: 88ee (88%); ee 888888°M.

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