All Notebooks | Help | Support | About
16th March 2014 @ 23:19

Repeat of AEW 95-3/JU 2-1 for scale up of key starting material for JU 3-6 (link!).

Reaction Scheme

Procedure

Started 3pm

JU 1-2 (crude, 1.034 g, 7.15 mmol) was stirred into a solution of AcOH (0.4 mL) and MeCN (12 mL). 4-formylbenzonitrile (0.938 g, 7.15 mmol) was added and the reaction was stirred at room temperature for 2.5 h. Analysis by TLC showed the reaction was complete as there was no JU 1-2 SM left.

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

The reaction mixture was left overnight and the solvent removed by rotary evaporation and dried in vacuo to yield a crude pale orange solid (1.742 g, 95%). The crude product was analysed by 1H NMR.

1H NMR, crude, DMSO, 200 MHz

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

Linked Posts
This post is linked by:
Attached Files
Reaction Scheme JU 2-1.png
TLC JU 2-2 30:70 EtOAc:Hex.jpg
JU 2-2 crude DMSO 200 MHz.pdf
JU 2-2 crude DMSO.zip