Ariffin, Azhar 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, DOI https://doi.org/10.1081/scc-200043164.
Full text not available from this repository.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 |
|---|---|
| Funders: | UNSPECIFIED |
| 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 > Department of Chemistry |
| Depositing User: | Miss Malisa Diana |
| Date Deposited: | 03 Jul 2013 09:03 |
| Last Modified: | 27 Aug 2019 06:07 |
| URI: | http://eprints.um.edu.my/id/eprint/8041 |
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