Science of Synthesis

Lawrence, S. A., Science of Synthesis, (2009) 40, 531.

The Gabriel synthesis of amines involves the reaction of a metal phthalimide, usually potassium phthalimide (‌72‌), with an organic halide and subsequent cleavage of the alkyl phthalimide ‌73‌ to release a primary amine ‌74‌ (‌Scheme 53‌; see also Houben–Weyl, Vol. 11/1, pp 79–96).[‌151‌–‌156‌] Cleavage of the N-alkylated phthalimide can be accomplished by acid- or base-catalyzed hydrolysis or by the Ing–Manske modification, which uses hydrazine hydrate in methanol or ethanol.[‌153‌]

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‌Meeeee 88‌ Meeeeeeee ee Meeeee ee eee Meeeeee Meeeeeee[‌888‌–‌888‌,‌888‌]

‌Meeeeeeeeee 88‌

e e.e. = eee eeeeeeee.

Mee eee ee eee Meeeeee eeeeeeeee eee eeee eeeeeeee ee eee eee ee Meeeeeeee eeeeeeeeee,[‌888‌] eee eeee ee eeeeeeeee-eeeeeeee eeeeeeeee ee eee eeeeeeee ee eeeeeeeee eeeeeeeee eee eeeeeeeeeeeeeeeeee eeeeeee ee e eeeeeeee.[‌888‌] Mee eee ee eeeee eeeeeeee eeeee[‌888‌] ee eeeeeeeeeee eeeee[‌888‌] ee eeeeeeeee eee eeee eeee eeeeeeee. Me eeeeeee ee eee Meeeeee eeeeeeee eeeeeeeee ee eeeeeeeeeeeeeeeeee eeeeeee ee eeeeeeeeeee ee Meeeeee ee Meeeeeeee, Mee. 8 [Meeeeeeee ee Meeee 8 (Me…Me) (Meeeeee ‌8.8.8.8.8‌)].

Mee Meeeeee eeeeeeee eee ee eeee ee e eeeeeeeee eeee ee eeeee ee eeee eeeeeee eeeeeeeee, eeee e eeee eeeee ee eeeeeee eeeeeeeeeeeeeee eeeee eeeeeeeee ee eee eeeeeeeee eeeeeeeeeee eeeeeeeeee eeeeee eeeeeeeeee ee eee eeeee. Meeeeeeeeeeee eeeee eeee eeeeeeeee eeeeeeeeeee ee eeee ee M-eeeeeeee eeeeeeeeee eeeeeeeeee eeeee eee eeee ee eeeeeee eeee eeeeeee eeeeeee. Meeeeeee eeeeeee eeeeeeee eeee ee eeeeeeee eeee eee e Meeeeee–Meeeee eeeeeeee,[‌888‌] eeee eee eeeeee eeee ee e eeeeeeee (eeeee eeeee eeeeeeeeeeeeeee eee eeeeeeeeee eeeee ee ω-eeeeeeeeeeeeeee eeee),[‌888‌–‌888‌] ee eeee eeeeeee eeeee ee eeee e eeeeeee (eee Meeeee–Meee, Mee. 88/8, e 88). Meee eeeeee eeeeeeee eeeeee eee eeeeeeeeeee ee eeee eeeeeeeeeeeee eeeeeeeeeee eeeeeeee.

Me eeeeeee eeeeeeeee ee eee Meeeeee eeeeeeee eeee 8,8-eeeeeeeeeeeee eeeeeeee eeeeeeee ee eee M-(8-eeeeeeeeee) eeeeee ‌88‌ eeee eeeeeeeee eeeeeeeee ee eee ee eee M—M eeeee ee eeee eeeeeeeee 8-[(8-eeeeeeeeee)eeeeeeeee]eeeeeeee (‌88‌). Meee eee eeee eeeeeee ee eeeeeeeeeeeeee eeeeeeeeeee ee eeee ee eeeee-eeeeeeee eeee ee eeeeeeee eeeee ‌88‌, eeeee eeeeeee ee eeeeeee eeeeee ee eeee 8-eeeeeeeeeeee (eeeeeeeeeeee) eee eeeeeeee eeee (‌Meeeee 88‌).[‌888‌–‌888‌]

‌Meeeee 88‌ Meeeeeeee ee 8-Meeeeeeeeeee ee eee Meeeeee Meeeeeee[‌888‌–‌888‌]

Me ee eeeeeeeeeee ee eeeee eeeeeeeeeeee, eeeeee eeeeeeeeeeeee (‌88‌) eeeeee eeee eeeee eeeeeee ee eeee ee eeeeeeeeeeeeeeee, eeeee ee eeee eeeeeeeeee ee eee eeeee ‌88‌ (‌Meeeee 88‌). Mee eeeeeeeeeeee eeeeeeeeeeeeeeee eee ee eeeeeeee, eee eee eeeeeeee eee eeee ee eeeeeeeee ee e eee-eee eeeeeeeee.[‌888‌]

‌Meeeee 88‌ Meeeeee-Meee Meeeeeeee Meeee e Meeeeeeeeee Meee[‌888‌]

Meeeeeeeeeeeeeeeee (‌88‌) ee eeeeeeeee ee eeeeeee eeeeeeeeeeee eeeee eeeee eeeeeee ee eeeeeeeeeeeeeeeee. Mee eeeeeeeeeeee M-eeeeeeeeeee ‌88‌ eee ee eeeeeeeee eeee eeeeeee eeeeee ‌88‌ ee eeeeeeee eeeeeeeeee ee ee eeeeeeeee (‌Meeeee 88‌).[‌888‌] Me eee eeeee eeee ee eee eeeeeeee, eeeeee eeeeeeeee eeeeeeeee eeeeeeee eeee eeeeeeeee eeeeeeeeee; eee eeeeeee, ee eee eeee ee eeeeeeeeeeeeeeee, eeeeeeeeeee ee eee eeee eeeeeee eeeeeeee (ee 88% eeeee).[‌888‌] Mee eeeeeeeeeeee M-eeeeeeeeeeeeeeeeeeeeeeee eee ee eeeeeee eeeeeee eeee eeeeee eeeeeee eee eeeeeee eeeee eeeeee eeeeee e eeeeeeeeeeeeeeee. Meeee eeeeeeee ee eee eeeee, ee eeeeeeeeeeeee eeeeeeeeeeee ee eeeeeeee. M-Meeeeeeeeeeeeeeeeeeeeeee eee eeee ee eeeeeeeee ee eeeeeee eeeee eeeeeeee ee eeeeeee ee eee eeeeeeee ee eeeeeeeee eeeeeee eee 88-eeeee-8 ee eeee ee M,M-eeeeeeeeeeeee eeeeeeeeeeeeeeeeee, eeeee eee ee eeeeeee ee eeeeeeeeee eeeeeeeee eeeeeeeee ee eeee ee eeeeeeeeeeeee eeeeeeeee eeeee (88–88%).[‌888‌]

‌Meeeee 88‌ Meeeeeeee ee Meeeeee Meeeee Meeee Meeeeeeeeeeeeeeeee[‌888‌]

‌Meeeeeeeeee 88‌

e e.e. = eee eeeeeeee.

Meeeeeeeeeee Meeeeeeee

Meeeeeeeeee (‌88‌, M8 = Me); Meeeeee Meeeeeeee:[‌888‌]

Me eeeeeeee eeeeeee ee eeeeeeeeeee (888 e, 8.88 eee) eee M8MM8 (888 e, 8.88 eee) eee eeeeeee eeee MeMe (888 e, 8.88 eee) eee eee eeeeeeeee eeeeeee eee eeeeee ee eeeeee eee 8 e. Meeeee MeMe eee eeeeeee ee eeeeeeeeeeee ee e eeeeeee ee eeeee eee eee eeeeeee eee eeeeeeeee ee eeeeeeeeee eee eeeeee eeee M8M ee eeee M-eeeeeeeeeeeeeeeee (‌88‌, M8 = Me); eeeee: 888–888 e (88–88%). Mee eeeeeeeeeeeeeeeee eeeee ee eeeeeeee ee eeeeeeeeeeeeeeeee (MeMM).

M eeeeeeeeee ee eeeeee eeeeeeee eeeeee eeeeeeeeeee (‌88‌, M8 = Me; 8 eee) ee MeMM eee eeeeee eeee M8MMM8•M8M (8 eee). Mee eeeee, eeeeeeeeee eeeeeeeeeee, eeeee eeeeee eeeeeee, eee eeeeeeeeee ee eeeeeee eeee eeeeee MMe. Mee eeeeeeeeeeee eeeeeeeee eeeeeeeee eee eeeeeee ee eeeeeeeeee eee eeeeee eeee M8M eee eee eeeeeeee eee eeeeeeee eeee eeeeeeeee eeeeeeeeeeee ee eeeeee MeMM. Mee eeeeeee eeeeeeeeeeee eeeeeeeee eeeeeeeee eee eeeeeee ee eeeeeeeeee. Mee eeeeeeee eee eeee eeee eeeeeeee eee eee eeeeeeeee eeee Me8M. Mee Me8M eeeeeeee eeee eeeee (MMM), eeeeeeeeeeee, eee eeeeeeeee; eeeee: 88–88%.

Meeeee ‌88‌; Meeeeee Meeeeeeee:[‌888‌]

M eeeeeee ee eee eeeeeeeeee eeeee (8.8 eee), MeM(MMM)8 (‌88‌; 88.8 e, 8.88 eee), eee MeMM (88 eM) eee eeeeee eeee eeeeeeee ee ee eeeeeeeee ee 88°M eee 8 e ee 888°M eee 8 e. Meeee MMe (88 eM) eee eeeee eee eee eeeeeee eee eeeeeeee eee 8 e. Mee eeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee eeeeeee eee eee eeeeeee eee eeeeeee eeee 88% ee MeMM eeee eeeeeee, eeeeeeeee eeee Me8M, eeeee (MMM), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Meeeeeeeeeee eee ee eeeeeeeeeeee.

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) 88/8, 88.
• 8.Meeeee-Meee, (8888) M 88e8, 888.