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NADZHAFOVA
2-Alkyl-1-(2-aminoethyl)pyrroles
were
also
added dropwise within 3 h 14.4 g (0.1 mol) of
obtained by treating 2-alkyl-1-(2-bromoethyl)pyrroles
with excess ammonia.
2,2 -dichlorodiethyl ether dissolved in 25 ml of di-
oxane. Then the reaction mixture was boiled for 4 h
more, cooled, washed with diluted solution of sodium
carbonate, the water layer was separated and ex-
tracted with ether, the combined ether solutions were
dried with MgSO4, and on removing the solvent the
residue was subjected to vacuum distillation.
EXPERIMENTAL
IR spectra were recorded on spectrophotometer
UR-20 from thin films of liquid substances and from
1
mulls in mineral oil of solids. H NMR spectra were
2-Alkyl-1-(2-acetoamidoethyl)pyrroles (IVa d).
To a solution of 0.025 mol of pyrrole II in 50 ml of
anhydrous ether was added dropwise at stirring
2.5 ml (0.025 mol) of acetic anhydride. Then the
reaction mixture was boiled for 4 h and on cooling
was washed with diluted solution of sodium carbonate,
the water layer was separated and extracted with
ether, the combined ether solutions were dried with
MgSO4, and on removing the solvent the residue was
subjected to vacuum distillation.
registered from 5 10% solutions of compounds
obtained in CCl4 or DMSO-d6 on spectrometer Tesla
BS-487B (80 MHz) using HMDS as internal refer-
ence. The purity of compounds obtained was checked
by GLC on chromatograph Chrom-3-JKZ (stationary
phase PMS-100 on Chromosorb W) and by TLC on
Silufol UV-254 plates. The initial ketones I were
prepared by procedure [5].
2-Alkyl-1-(2-aminoethyl)pyrroles (IIa d)
(Table 1). (a) To a mixture of 25.7 g (0.3 mol) of
70% water solution of ethylenediamine and 100 ml
of ether at 15 20 C was added dropwise while stir-
ring a solution of 0.1 mol of 3-chloro-1-propenyl
alkyl ketone or 2-methoxy-3-chloropropyl alkyl
ketone in 50 ml of ether. Then the reaction mixture
was boiled for 6 h. On cooling the ether layer was
separated, washed with water, the water layer was
extracted with ether. The combined ether solutions
were dried on MgSO4, the solvent was distilled off,
and the residue was subjected to vacuum distillation.
N-(2-Methylpyrrol-1-yl)ethylmaleinamic-
(phthalamic) acid (Va, b). To a solution of 0.05 mol
of the corresponding acid anhydride in 50 ml of
acetone at 20 25 C while stirring was added drop-
wise 6.8 g (0.055 mol) of pyrrole IIa dissolved in 50
ml of acetone. Then the reaction mixture was stirred
at room temperature for 3 h, the crystals formed were
filtered off, washed with ether, and recrystallized
from heptane.
N-(2-Methylpyrrol-1-yl)ethylmale(phthal)imide
(VIa, b). (a) A solution of 0.025 mol of the cor-
responding acid anhydride and 3.4 g (0.027 mol) of
pyrrole IIa in 50 ml of DMF was boiled for 5 h. On
cooling the reaction mixture was poured into ice
water, and the mixture was left standing for 2 h. The
separated crystals were filtered off, washed with
water, died, and recrystallized from heptane.
(b) To a mixture of 30 ml (0.4 mol) of 25% water
solution of ammonia and 50 ml of ether at 25 30 C
was added dropwise while stirring a solution of
0.1 mol of 2-alkyl-1-(2-bromoethyl)pyrrole in 50 ml
of ether. Then the reaction mixture was boiled for 5 h
and further it was worked up as above. According to
1H NMR and IR spectra, boiling points, and refractive
indices the compounds obtained were identical to
pyrrole derivatives synthesized by procedure a.
(b) A mixture of 0.025 mol of acid Va, b and
50 ml of DMF was boiled for 3 h. The workup and
purification of the product was done as above.
2-Alkyl-1-(2-morpholinoethyl)pyrroles (IIIa d).
A solution of 0.1 mol of pyrrole II and 28 ml
(0.2 mol) of triethylamine in 100 ml of dioxane was
brought to boiling, and then at vigorous stirring was
1
According to H NMR and IR spectra and boiling
points the imides of dicarboxylic acids prepared by
procedures (a) and (b) were identical.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 38 No. 6 2002
Nadzhafova
