Supporting Information

Contents
Page No.

1. General……………………………………………………………………14-15
2. Spectra of the compounds …………………............................................. 16-18
1. General
Chemicals and Apparatus:

All the chemicals used were of research grade (purchased from Sigma Aldrich and Acros)
and used without further purification. The melting points of all compounds were
determined on a Toshniwal apparatus in capillary and uncorrected. IR spectra were
recorded on a Shimadzu FT IR- 8400S spectrophotometer. 1H and 13C NMR spectra were
obtained using CDCl3 as solvent on a JEOL JNM LA-300 spectrometer (300 MHz for 1H
NMR and 75 MHz for 13C NMR). The 1H NMR data were reported as follows in ppm (δ
) from the internal standard (TMS, 0.0 ppm), chemical shift (multiplicity, coupling
constant in Hz, integration), and the 13C NMR data in ppm (δ ) from the internal standard
(TMS, 0.0 ppm). Mass spectra were obtained using Waters Xevo G2S instrument.

General procedure for the preparation of the imidazolium based ionic liquids:

To a stirred solution of 1-methylimidazole (8.91 g, 100.0 mmol) in acetonitrile (70 mL)

was added butyl bromide ( 110.0 mmol) dropwise at 00C. The reaction mixture was stirred
for 24-48 h at 30 0C. Removal of the solvent under reduced pressure afforded crude 1-
butyl-3- methylimidazolium bromide. Completion of all the reactions was confirmed by
1 13
H and C NMR. The crude product was used without further purification for the next
step, the anion metathesis.

General procedure for anion metathesis:

To a solution of the crude 1-butyl-3-methylimidazoliumbromide, obtained from the above
reactions, in acetone (70 mL) was added hexafluorophosphoric acid (10.90 g, 100.0
mmol). The reaction mixture was stirred for 24 h at room temperature. The resulting
mixture was filtered. Evaporation of the solvent under reduced pressure afforded the
corresponding 1-Butyl-3-methylimidazolium hexafluorophosphate. Same procedure was
used except that trifluoro methane sulphonic acid (15.08 g, 100.0 mmol) was used instead
of hexafluorophosphoric acid. The resulting mixture was filtered. Evaporation of the
solvent under reduced pressure afforded the corresponding imidazolium trifluromethane
sulphonate.1-Butyl-3-methylimidazolium tetrafluoroborate was also prepared using the
same procedure as above except that tetrafluoro boric acid (15.08 g, 100.0 mmol) was
used in place of hexafluorophosphoric acid. Progress of the reaction was measured by
TLC. Completion of the reaction was confirmed by 1H NMR.
General procedure for the synthesis of Quinoxalines:
A mixture of aromatic diamine derivatives (2 mmol) and a 1,2- dicarbonyl compound (2
mmol) in ionic liquid (2 mL) was stirred at room temperature for the appropriate time.
The progress of the reaction was monitored by TLC (n-Hexane: EtOAc, 7:3), after
completion of the reaction, the reaction mixture was diluted with water and extracted using
diethyl ether (3x10ml). The combined organic layer was dried over anhydrous sodium
sulphate and evaporated under reduced pressure to afford the corresponding product. The
residual ionic liquid was dried under vacuum and reused. The same procedure was
repeated for the reaction of aromatic anilines with isatin and acenaphthoquinone and
phenaacyl bromide. All the products obtained were characetrised by IR, 1HNMR,
13
CNMR and Mass studies.
 5 4
N+
N
F 2O
F
S O
F O

Fig. 1: 1H NMR spectrum of [Bmim]CF3SO3

5 4
N+
N
F 2O
F
S O
F O

Fig. 2: 13C NMR spectrum of [Bmim]CF3SO3

N

Fig. 3: 1H NMR spectrum of 6g

Fig. 4: 13C NMR spectrum of 6g

N

Fig. 5: 1H NMR spectrum of 5b

Fig. 6: Extended 1H NMR spectrum of 5b

 N

Fig. 7: 13C NMR spectrum of 5b

[M+H]+
.

N N
H

Fig. 8: MS spectrum of 4b
 N

N N
Br H
M+H2O

Fig. 9: MS spectrum of 4g

[M+H]+
.

Fig. 10: MS spectrum of 6g

 [M+H]+
.

Fig. 11: MS spectrum of 3c

[M+H]+
.
N

Fig. 12: MS spectrum of 5c

[M+H]+
.
N

Fig. 13: MS spectrum of 3a