D
P. C. Glowacka, G. R. Stephenson
Letter
Synlett
Generally, reactions in DCE were noticeably faster than
those carried out in EtOH, MeOH, THF, or MeCN for all re-
ducing agents (e.g., Table 1, entry 3; Table 2, entry 3; Table
3, entry 3). However, the yields were improved from 0% to
27% and 40%, respectively, when the reactions were carried
out with reducing agents in anhydrous MeOH (Table 1, en-
try 2; Table 2, entry 2, Table 3, entry 2).
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Overall, the best conditions were achieved by using
NH4Cl as a source of nucleophile and NaBH4 as the reducing
agent in dry DCE at room temperature.
The results presented here indicate that sodium borohy-
dride is a synthetically useful reagent for reductive amina-
tion of 9-aldehydeanthracene with ammonium chloride. It
is a mild, inexpensive, nonhazardous, and commercially
available reagent, and it is a reagent of choice for reductive
amination of many carbonyl compounds. Additionally it is a
‘greener’ choice of reducing agent when compared to
NaBH3CN. In representative comparisons with other com-
monly used reducing reductive amination reagents, sodium
borohydride reacted consistently faster, gave better yields,
and produced fewer side products. DCE allows a rapid for-
mation of imines from aldehyde and amine to isolate the
target molecule in 80%.
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Acknowledgment
(16) Hosseinzadeh, R.; Golchoubian, H.; Nouzarian, M. Res. Chem.
Intermed. 2015, 41, 4713.
We thank the EU Interreg IV Trans Manche/Channel cross-border
project ‘Innovative Synthesis: Chemistry and Entrepreneurship’
(IS:CE chem: ref. 4061) for financial support.
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