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15th October 2014 @ 10:32

Conclusion: Final product yield of 97%, no column purification required, nice reaction. 


Reaction Scheme 

Procedure

6-Chloropicolinic acid (1000 mg, 6.35 mmol) in thionyl chloride (10ml) was stirred and
heated to reflux for 1 hour. The excess thionyl chloride was evaporated in vacuo and dichloromethane (15 mL) was added to the residual 6-chloropicolinoyl chloride.  A solution of 3-chloroaniline (0.67 mL, 6.35 mmol) and triethylamine (0.89 mL, 6.35 mmol) in dichloromethane (7 mL) was added dropwise with stirring, maintaining the temperature below 20° C by submerging the flask in an ice-water bath.  After the addition, the reaction mixture was stirred ovenight at an ambient temperature. Water (10 mL) was then added to the solution and the phases were separated. The water layer was washed with dichloromethane and the organic layers were combined. The organic layer was washed with 0.1 M HCl (10 mL) and then separated before being dried over MgSO4. The solvents were then removed in vacuo to yield the target compound as a yellow solid ( 1.65 g, 6.17 mmol, 97% yield). 

 

Risk Assessment 


JS 1-1.docx

InChI strings

InChI=1S/C6H4ClNO2/c7-5-3-1-2-4(8-5)6(9)10/h1-3H,(H,9,10)

to

InChI=1S/C12H8Cl2N2O/c13-8-3-1-4-9(7-8)15-12(17)10-5-2-6-11(14)16-10/h1-7H,(H,15,17)

SMILES

ClC1=NC(C(O)=O)=CC=C1

to

ClC1=NC(C(NC2=CC=CC(Cl)=C2)=O)=CC=C1

 

NMR 

JS 1-1 crude.pdf

 

Mass Spec

JS 1-1(2).jpg

 

JS 1-1(1).jpg
Attached Files
JS 1-1 new.png
JS 1-1.docx
JS 1-1 crude.pdf
JS 1-1(2).jpg
JS 1-1(1).jpg