Synthesis of pyrrole derivative from amino gp

synthesis of pyrrole derivative from amino gp,

MAKES ORG CHEM, GOOD RESEARCH PROJECT

Paal-Knorr reaction of aniline and 2,5-diketone1-Phenyl-2,5-Dimethylpyrrole

 Reaction Scheme: Paal-Knorr reaction of aniline and 2,5-diketone

Procedure

To a 250 mL one-necked round bottom flask equipped with stir bar was added aniline (2.79 g, 0.030 mol), 2,5-Hexanedione (3.65 g, 0.032 mol), and toluene (75 mL, 0.4 M in aniline). Upon mixing for 5 minutes, p-TsOH (0.114 g, 0.0006 mol) was added all at once. The flask was then equipped with a Dean-Stark trap and reflux condenser. The solution was heated to reflux (≈120oC). for 1 houra. After this time the flask was cooled to room temperature and the solution was  transferred to a 500 mL separatory funnel. The organic layer was washed with a saturated sodium bicarbonate solution (2 X 100 mL), deionized water (2 X 100 mL), and finally with brine (2 X 100 mL).  The organic layer was dried with Na2SOand the solvent was removed by rotary evaporation to afford a greenish solidb,c (3.69 g, 72%). 

Notes:
a.  By this time approximately  one equivalent (based on aniline) of water had condensed into the Dean-Stark trap. 
b. This was judged to be pure by GC-MS and NMR analysis
c. Despite these colorations, their GC-MS and NMR data agreed with literature data

Data

1H NMR (CDCl3, 300 MHz) δ ppm 2.03 (s, 3 H) 5.91 (s, 2 H) 7.19-7.22-(m, 2 H) 7.38-7.47 (m,3 H) 7.37 (d, J=8.80 Hz, 2 H) 
13C NMR (CDCl3, 75 MHz) δ ppm 13.12 (CH3) 105.82 (CH) 127.72 (C) 128.36 (CH) 128.83 (CH) 129.15 (CH)  139.15 (C)

Thiemann, F.; Piehler, T.; Haase, D.; Saak, W.; Lützen A. Eur. J. Org. Chem. 2005, 1991.

 

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