Suggested improved method for the ing-manske and related reactions for the second step of gabriel synthesis of primary amines

Ariffin, A. and Yun, C.S. and May, F.Y. and Khan, M.N. and Lan, L.C. (2004) Suggested improved method for the ing-manske and related reactions for the second step of gabriel synthesis of primary amines. Synthetic Communications, 34 (24). pp. 4439-4445. ISSN 0039-7911

Full text not available from this repository. (Request a copy)
Official URL: http://www.tandfonline.com/doi/pdf/10.1081/SCC-200...

Abstract

This work demonstrates an improvement in the Ing-Manske and related procedures by the increase of pH of the reaction mixture after the complete disappearance of N-substituted phthalimide. Hydrazinolysis of N-phenylphthalimide (1a) gave 80% of the desired primary amines after 5.3 h in the absence of added NaOH. The reaction time was reduced to 1.6 h and 1.2 h when 1 eq. and 5 eq. of NaOH were added to the reaction mixture after the complete disappearance of 1a. Hydroxyaminolysis of N-(4-ethylphenyl)phthalimide (1b) gave 80% of the desired primary amines after 7.5 h of reaction time (at added [NaOH] = 0). When 10 eq. and 20 eq. of NaOH were added to the reaction mixture after the disappearance of 1b, the reaction time was reduced to 4 h and 2 h, respectively. Methylaminolysis of N-(2-ethylphenyl)phthalimide (1c) gave 80% of the desired primary amines after 1.7 h (at added [NaOH] = 0). The reaction time was reduced to 1 h and 0.7 h when 1 eq. and 25 eq. of NaOH were added to the reaction mixture after the complete disappearance of 1c.

Item Type: Article
Additional Information: Department of Chemistry, Faculty of Science Building, University of Malaya, 50603 Kuala Lumpur, MALAYSIA
Uncontrolled Keywords: gabriel synthesis, ing-manske procedure, n-substituted phthalimides, aminolysis, acids
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Science > Dept of Chemistry
Depositing User: Miss Malisa Diana
Date Deposited: 03 Jul 2013 09:03
Last Modified: 03 Jul 2013 09:03
URI: http://eprints.um.edu.my/id/eprint/8041

Actions (login required)

View Item View Item