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Antoncho
(Official Hive Translator)
07-12-02 18:31
No 331743
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Canizzaro reduction of subst'd benzaldehydes
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For the ones who prefer reducing nitriles (hydrazine hydrate over Raney Ni gives excellent results - has it ever been posted?) to reducing nitrostyrenes. Convertion of a PhCHO to BzOH via Canizzaro rxn (then treated w/HCl and KCN) as described on Rh's site.<br><br><img src="../picproxie_docs/000331743-file_yut6.gif"><br><br><a href="http://l2.espacenet.com/dips/viewer?PN=GB627769&CY=gb&LG=en&DB=EPD" target="_blank" title="Jump to this patent">Patent GB627769</a><br><br><br>Antoncho
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Tricky<br>
<i>(<span title="The user's title at the time of posting">Stunning</span>)</i><br>
<span title="Posting date">08-22-02 19:22</span><br>
<span title="Link to this post by using the markup [347725]">No 347725</span><br>
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<b title="The subject of this post">Nitriles reduction.</b><br>
<i title="This post has been up-rated by the moderators">(Rated as: excellent)</i>
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Hmmmm. <br>Last time I'm crazy about reduction of nitriles, cause I find a simple ways to 2C-substantions...<br>So, what do I know about nitriles???<br>After that I UTFSEd I found only one post I've like, this post, there Antoncho mentioned about reduction of nitriles over Raney nickel with great yield... <br>Antoncho, it seems noonebee observed you said... Let's try to improve it <img src="../forum/images/icons_lightgrey/wink.gif" alt="wink" title="Wink" heigth="15" width="15"><br>So, what do I know about nitriles???<br><br>Triptamine synthesis (quoted from Khimicheskaja nauka i promyshlennostj, 1959,4, N2,281-282).<br><b>Nitrile reduction with Hydrazine hydrate over Raney-Nickel</b><br><font color="blue">Here mentioned, this method works with benzylcyanides too</font color="blue"><br>To mixture of 0,016mol of 3-indolylacetonitrile, 0,5g of Raney-Nickel catalist and 50ml of ethanol, 48ml of hydrazine hydrate was added by small portions. After addition was completed, mixture was heated to 100C. Heating was continued until the NH<sub>3</sub>-isolation bring to a stop. Catalist was filtered off and ethanol was evaporated in vacuo. <br>Result - 2,4g of triptamine, yield is 95%.<br>Enjoy.<br><br>BTW, does somebee knows, will the Mannich rxn work with 2,5-DMBA (to produce 2,5-dimethoxy-4-N,N-dimethylaminomethylb<wbr>enzaldeh<wbr>yde)??? <wbr> <br>Thanx.<br><br><hr>There's a hole in our soul that we fill with dope <br>And we're feeling fine. <br>
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<font color="#FF0033">Rhodium</font><br>
<i>(<span title="The user's title at the time of posting">Chief Bee</span>)</i><br>
<span title="Posting date">09-02-02 12:03</span><br>
<span title="Link to this post by using the markup [351755]">No 351755</span><br>
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<b title="The subject of this post">No, the Mannich reaction only works with phenols.</b>
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No, the Mannich reaction only works with phenols.
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