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16th October 2013 @ 04:24

AEW 86-1 (1.91 g, 13.2 mmol) was sirred in AcOH (0.64 mL) in MeCN (19.2 mL) and 4-formylbenzonitrile (1.73 g, 13.2 mmol) was added to the orange suspension and the resulting reaction mixture stirred at room temperature for 2 h. No SM visible on TLC, but no clear product spot either. The solvent was removed under vacuo to yield an orange/brown solid (4.04 g, 15.7 mmol, 120% crude yield) still MeCN present and peaks that could be SM, no aldehyde, pretty insoluble in CDCl3 but no SM on TLC plates suggesting E and Z isomers.

Some crude material (500 mg) to be submitted to AEW 97-1, the rest retained for possible purification.

TLC (30% EtOAc in Hexane and 100% EtOAc, under UV then stained with ninhydrin)

AEW 95-2 UV 30%EtOAc in Hex.JPG
AEW 95-2 Ninhydrin 30%EtoAcinHex.JPG
AEW 95-2 UV (EtOAc).jpeg
AEW 95-2 Ninhydrin 100% EtOAc.JPG

1H NMR (400 MHz NMR)

zoomed to aromatic region

AEW 95-2 crude 400MHz Proton.pdf

Photo of 500 mg of crude material as submitted to AEW 97-1

AEW 95-2 crude material.JPG

Hazard and Risk Assessment:

HIRAC AEW 95-2.pdf

InChi:

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+

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Attached Files
HIRAC AEW 95-2.pdf
AEW 95-2 crude material.JPG
AEW 95-2 crude 400MHz Proton.pdf
AEW 95-2 Ninhydrin 30%EtoAcinHex.JPG
AEW 95-2 UV (EtOAc).jpeg
AEW 95-2 UV 30%EtOAc in Hex.JPG
AEW 95-2 Ninhydrin 100% EtOAc.JPG