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Author: Subject: 1-methyl-lysergic acid preparation
Query
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[*] posted on 30-8-2011 at 12:37
1-methyl-lysergic acid preparation

5g methysergide (1-Methyl- d-lysergic acid- (1-hydroxybut- 2-yl) amide) is dissolved in 50 mL 10% aqueous NaOH solution. This mixture is refluxed under argon at 50 degrees Celsius for 4 hours. The mixture is cooled to RT, there is then added 50 mL of a 10% tartaric acid aqueous solution upon which crystals precipitated. These solids were removed by filtration, washed with water and dried to constant weight.

Would you guess that this compound would be
A) Lysergic acid/isolysergic acids
B) 1-methyl lysergic acid
?
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Nicodem
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30-8-2011 at 13:33
UKnowNotWatUDo
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[*] posted on 30-8-2011 at 14:35


B

Normally I wouldn't answer a question like this but I'm bored and in a good mood.
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Query
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[*] posted on 30-8-2011 at 15:15


Any ideas on how to demethylate?

Thionyl Chloride maybe?

[Edited on 30-8-2011 by Query]
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mr.crow
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[*] posted on 31-8-2011 at 11:43


Another Stupid Thread! Detritus



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UKnowNotWatUDo
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[*] posted on 31-8-2011 at 13:20


What leads you to believe that thionyl chloride would demethylate the nitrogen? Show me you have a slight grasp of the reactions and that you're willing to put in some time researching. If you actually spend some time looking around U2U me.
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jon
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[*] posted on 3-9-2011 at 12:03


you should have transesterified the amide with methanolic hydrogen chloride



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jon
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[*] posted on 3-9-2011 at 12:05


1 in the numbering system of ergolines implies the carbon adjacent to the indole ring for example



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[*] posted on 3-9-2011 at 13:58


I believe you're mistaken about the placement of the 1-methyl group. In methysergide it is on the indole nitrogen.
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