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12th May 2014 @ 07:12

Repeat of JU 2-3 for scale up of key starting material.

Reaction Scheme

Procedure

Started

JU 1-6 (crude, 6.99 g, 48 mmol) was stirred into a solution of AcOH (2.8 mL) and MeCN (84 mL). 4-formylbenzonitrile (5.0 g, 38 mmol, 0.8 equiv) was added and the reaction was stirred at room temperature for 15.5 h. Analysis by TLC showed the reaction was complete.

TLC JU 2-4 30:70 EtOAc:Hex 15.5 h.jpg

The solvent was removed by rotary evaporation and the product dried in vacuo. The crude product was orange in colour (x g, x% crude yield) and was analysed by 1H NMR.

1H NMR, crude, DMSO, 200 MHz

JU 2-4 crude DMSO 200 MHz.pdf
JU 2-4 crude DMSO.zip

The 1H NMR does not show the characteristic N-H peak at 11.8 ppm, however all other expected peaks are the same as for previous attempts of the experiment. 50 mg of JU 2-4 will be put into a cyclisation reaction and monitored by TLC to check if product forms (see JU 3-1 for HIRAC). Further analysis by LRMS and HRMS will also be carried out. An NMR experiment using 5 mg of JU 2-3 and 5 mg JU 2-4 will also be conducted to determine if the compounds are the same.


IR data

JU 2-4.pdf

 

HIRAC

See JU 2-1

InChI strings

InChI=1S/C4H5ClN4/c5-3-1-7-2-4(8-3)9-6/h1-2H,6H2,(H,8,9)

and

InChI=1S/C8H5NO/c9-5-7-1-3-8(6-10)4-2-7/h1-4,6H

to

InChI=1S/C12H8ClN5/c13-11-7-15-8-12(17-11)18-16-6-10-3-1-9(5-14)2-4-10/h1-4,6-8H,(H,17,18)/b16-6+

SMILES

ClC1=CN=CC(NN)=N1

and

[H]C(C1=CC=C(C#N)C=C1)=O

to

ClC1=CN=CC(N/N=C/C2=CC=C(C#N)C=C2)=N1


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Attached Files
Reaction Scheme JU 2-1.png
TLC JU 2-4 30:70 EtOAc:Hex 15.5 h.jpg
JU 2-4 crude DMSO 200 MHz.pdf
JU 2-4 crude DMSO.zip
JU 2-4.pdf