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2nd April 2014 @ 02:16

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

Reaction Scheme

Procedure

Started 1pm

JU 1-4 (crude, 1.677 g, 11.60 mmol) was stirred into a solution of AcOH (0.6 mL) and MeCN (18 mL). 4-formylbenzonitrile (1.524 g, 11.60 mmol) was added and the reaction was stirred at room temperature for 4.5 h. Analysis by TLC showed the reaction was complete as all of JU 1-4 had been used. TLC showed an excess of the aldehyde. NB to avoid this next time, use 0.8 of an equivalent and only add more if needed.

TLC JU 2-3 30:70 EtOAc:Hex.jpg

The solvent was removed by rotary evaporation and the product dried in vacuo. The crude product was pale orange in colour (3.036 g, 102% crude yield, probably due to excess aldehyde remaining as seen in TLC) and was analysed by 1H NMR.

1H NMR, crude, DMSO, 200 MHz

JU 2-3 crude DMSO 200 MHz.pdf
JU 2-3 crude DMSO.zip

 

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 2-3 30:70 EtOAc:Hex.jpg
JU 2-3 crude DMSO 200 MHz.pdf
JU 2-3 crude DMSO.zip