Suggested improved method for the ing-manske and related reactions for the second step of gabriel synthesis of primary amines
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...
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2004
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my.um.eprints.80412019-08-27T06:07:27Z http://eprints.um.edu.my/8041/ Suggested improved method for the ing-manske and related reactions for the second step of gabriel synthesis of primary amines Ariffin, Azhar Yun, C.S. May, F.Y. Khan, M.N. Lan, L.C. QD Chemistry 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. 2004 Article PeerReviewed 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 http://www.tandfonline.com/doi/pdf/10.1081/SCC-200043164 10.1081/scc-200043164 |
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QD Chemistry Ariffin, Azhar Yun, C.S. May, F.Y. Khan, M.N. Lan, L.C. Suggested improved method for the ing-manske and related reactions for the second step of gabriel synthesis of primary amines |
| description |
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. |
| format |
Article |
| author |
Ariffin, Azhar Yun, C.S. May, F.Y. Khan, M.N. Lan, L.C. |
| author_facet |
Ariffin, Azhar Yun, C.S. May, F.Y. Khan, M.N. Lan, L.C. |
| author_sort |
Ariffin, Azhar |
| title |
Suggested improved method for the ing-manske and related reactions for the second step of gabriel synthesis of primary amines |
| title_short |
Suggested improved method for the ing-manske and related reactions for the second step of gabriel synthesis of primary amines |
| title_full |
Suggested improved method for the ing-manske and related reactions for the second step of gabriel synthesis of primary amines |
| title_fullStr |
Suggested improved method for the ing-manske and related reactions for the second step of gabriel synthesis of primary amines |
| title_full_unstemmed |
Suggested improved method for the ing-manske and related reactions for the second step of gabriel synthesis of primary amines |
| title_sort |
suggested improved method for the ing-manske and related reactions for the second step of gabriel synthesis of primary amines |
| publishDate |
2004 |
| url |
http://eprints.um.edu.my/8041/ http://www.tandfonline.com/doi/pdf/10.1081/SCC-200043164 |
| _version_ |
1643688201598009344 |
| score |
13.250246 |