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9th January 2013 @ 02:33

Reaction Scheme

4-nitroaniline (1 g, 7.24 mmol, 1.1 equiv.) and 2,5-hexanedione (0.77 mL, 6.58 mmol, 1 equiv.) were heated to 110 °C (oil bath temp.) for 4 hours. The reaction mixture was heterogeneous and no reaction was observed by TLC. Acetic Acid (3 mL) was added and the reaction mixture stirred at 110 ˚C for 16 hours. TLC showed reaction to be complete. The reaction mixture was allowed to cool and then pH changed to 5 by addition of an saturated aqueous solution of sodium hydrogen carbonate. Aqueous was extracted with EtOAc, washed with brine, dried (MgSO4), filtered and evaporated to give an orange brown oil that was purified by flash column chromatography over silica (5–20% EtOAc in Petroleum Ether) to obtain the desired product (1.22 g, 5.46 mmol, 83% yield) as a mustard coloured solid.

TLC:

AEW 35-1 20 h.jpg
AEW 35-1 4 hours.jpg


1H and 13C NMR:

AEW 35-1.pdf
AEW 35-1 carbon.pdf
AEW 35-1.zip


Hazard and Risk Assessment:

As for: Repeat Preparation of 1-(4-Fluoro-phenyl)-2,5-dimethyl-1H-pyrrole (AEW 1-1) but using: 

4-nitroaniline; risk class 2; HU and Sl; toxic by inhalation, in contact with skin and if swallowed, danger of culmulative effects, and harmful to aquatic organisms.

and:

Acetic Acid, risk class 2, HU and M, flammable and causes severe burns.

InChI=1S/C12H12N2O2/c1-9-3-4-10(2)13(9)11-5-7-12(8-6-11)14(15)16/h3-8H,1-2H3

See Also:

Synthesis of 1-(4-methoxyphenyl)-2,5-dimethyl-1H-pyrrole (AEW 36-1)

Synthesis of 4-(2,5-dimethyl-1H-pyrrol-1-yl)phenol (AEW 37-1)

Synthesis of 3-(2,5-dimethyl-1H-pyrrol-1-yl)benzenesulfonic acid (AEW 38-1)

Synthesis of 1-(benzo[d][1,3]dioxol-5-yl)-2,5-dimethyl-1H-pyrrole (AEW 39-1)

Synthesis of 2-(2,5-dimethyl-1H-pyrrol-1-yl)pyridine (AEW 40-1)

Synthesis of 3-(2,5-dimethyl-1H-pyrrol-1-yl)pyridine (AEW 41-1)

Synthesis of 4-(2,5-dimethyl-1H-pyrrol-1-yl)pyridine (AEW 42-1)

Synthesis of 2-(2,5-dimethyl-1H-pyrrol-1-yl)pyrimidine (AEW 43-1)

Synthesis of 2,5-dimethyl-1-phenyl-1H-pyrrole (AEW 44-1)

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Attached Files
AEW 35-1.png
AEW 35-1 20 h.jpg
AEW 35-1 4 hours.jpg
AEW 35-1 carbon.pdf
AEW 35-1.pdf
AEW 35-1.zip