Organic Process Research & Development
Communication
mol, 13% w/w) was added to another container. Both solutions
were fed into a T-shaped micromixer M1 at a total flow rate of
(11) (a) Green, A. Chem. Ind. 1998, 168. (b) Allian, A. D.; Richter, S.
M.; Kallemeyn, J. M.; Robbins, T. A.; Kishore, V. Org. Process Res. Dev.
2
011, 15, 91. (c) Gooden, P. N.; Bourne, R. A.; Parrott, A. J.;
Bevinakatti, H. S.; Irvine, D. J.; Poliakoff, M. Org. Process Res. Dev.
010, 14, 411.
12) (a) Jahnisch, K.; Hessel, V.; Lowe, H.; Baerns, M. Angew. Chem.,
Int. Ed. 2004, 43, 406. (b) Stevens, J. G.; Gomez, P.; Bourne, R. A.;
1
50 mL/min by using P (volume/flow rate: 480 mL/109 mL/
1
min) and P (volume/flow rate: 180 mL/41 mL/min) pumps,
2
2
(
and the outlet M1 was connected to another micromixer M2
which was connected with quenching agent hypochlorite
solution (40 g in 200 mL of water) and was fed by using
́
Drage, T. C.; George, M. W.; Poliakoff, M. Green Chem. 2011, 13,
another pump P (flow rate: 50 mL/min). After that the
3
2727.
outcome product 1c was collected and treated with charcoal
(13) Kawaguchi, T.; Miyata, H.; Ataka, K.; Mae, K.; Yoshica, J. Angew.
(
20 g). Subsequently, the charcoal was removed by filtration,
Chem., Int. Ed. 2005, 44, 2413. (b) Lev
Lett. 2011, 13, 5008.
14) Brechtelsbauer, C.; Lewis, N.; Oxley, P.; Ricard, F. Org. Process
Res. Dev. 2001, 5, 65.
15) Taghavi-Moghadam, S.; Kleemann, A.; Golbig, K. G. Org.
Process Res. Dev 2001, 5, 652.
́
esque, F.; Seeberger, P. H. Org.
and the filtrate solution was washed with toluene (100 mL).
Afterward the filtrate solution was cooled to 0−5 °C, and the
pH was adjusted to 8.0−8.5 by using acetic acid (∼30 mL).
Then the isolated solid was filtered and dried to obtain the
crude 1c in 88.2% yield (108.6 g) with 98.7% HPLC purity.
After that, crude 1c was recrystallized from acetone (350 mL)
to obtain the pure 1c in 85.1% yield (92.4 g) with 99.5% HPLC
purity.
(
(
(
(
16) Anderson, N. Org. Process. Res. Dev. 2001, 5, 613.
17) (a) Ratner, D. M.; Murphy, E. R.; Jhunjhunwala, M.; Snyder, D.
A.; Jensen, K. F.; Seeberger, P. H. J. Chem. Soc., Chem. Commun. 2005,
1
0, 578. (b) Tundo, P. Continuous Flow Methods in Organic Synthesis;
Prentice Hall PTR: Upper Saddle River, NY, 1992. See also: Moulijn,
J. A.; Makkee, M.; Van Diepen, A. Chemical Process Technology; Wiley:
Chichester, 2001. Third International Conference on Process Intensifica-
tion for the Chemical Industry; Green, A., Ed.; Professional Engineering
Publishing: Suffolk, 1999.
AUTHOR INFORMATION
Corresponding Author
■
(18) Rouhi, A. M. Chem. Eng. News 2004, 82, 18.
Notes
(19) (a) Prous, J. R. Drugs News Perspect. 1988, 1, 38. (b) Barradell,
L. B.; Faulds, D.; McTavish, D. Drugs 1992, 44, 225. (c) Sachs, G.;
Shin, J. M.; Howden, C. W. A. Pharmacol Ther. 2006, 23, 2. (d) Blaser,
H. U.; Schmidt, E., Eds.; Wiley-VCH: Weinheim; 2004, 413.
§
DRL-IPD Communication number: IPDO-IPM-00326.
The authors declare no competing financial interest.
(
20) (a) Akira, N.; Yoshitaka, M. U.S. Patent 4,628,098, 1986.
ACKNOWLEDGMENTS
■
(
(
b) Kohl, B.; Sturm, E.; Rainer, G. U.S. Patent 4,758,579, 1988.
b) Mahale, R. D.; Rajput, M. R.; Maikap, G. C.; Gurjar, M. K. Org.
Process Res. Dev. 2010, 15, 1264.
(21) (a) Gangula, S.; Elati, R. R. C.; Neredla, A.; Baddam, S. R.;
Neelam, U. K.; Bandichhor, R.; Dongamanti, A. Org. Process Res. Dev.
We thank the management of Dr. Reddy’s Laboratories Ltd. for
supporting this research work. Mr. G. Sharathchandra Reddy
thanks DRL for allowing him to pursue this work as part of his
summer training program.
2
010, 14, 229. (b) Kotagiri, V. K.; Vankawala, P. J.; Neelam, U. K.;
Baddam, S. R.; Elati, R. R. C.; Kolla, N. K.; Dayabhai, J. L.; Pingili, R.
R.; Gangula, S.; Jonalagadda, V. R.; Thakur, P.; Neredla, A.; Kammili,
V. R. WO/2008/045777, 2008.
REFERENCES
■
(
8
1) Zhang, X.; Stefanick, S.; Villani, F. J. Org. Process Res. Dev. 2004,
, 455.
2) Ducry, L.; Roberge, D. M. Angew. Chem., Int. Ed. 2005, 44, 7972.
3) Kawaguchi, T.; Miyata, H.; Ataka, K.; Mae, K.; Yoshica, J. Angew.
Chem., Int. Ed. 2005, 44, 2413.
4) Mason, B. P.; Price, K. E.; Steinbacher, J. L.; Bogdan, A. R.; Mc
Quade, D. T. Chem. Rev. 2007, 107, 2300.
5) Graham, C.; Zanfir, M.; Gavriilidis, A. Org. Process Res. Dev. 2006,
0, 539.
6) (a) Elati, R. C.; Kolla, N.; Gangula, S.; Naredla, A.; Vankawala, J.
(
22) Nagaki, A.; Manabu, T.; Suga, S.; Aoki, N.; Mae, K.; Yoshida, J.
J. Am. Chem. Soc. 2005, 127, 11666.
23) (a) Gibbard, L. Spinning Disc Reactors: New Opportunities for
(
(
(
the Chemical Industry. InProceedings of Process Intensification: Profits for
the Chemical Industry; Rotterdam, May, 1998. (b) Turunen, L.
Intensification of the Anthraquinone Process for Production of
Hydrogen Peroxide. In Proceedings of Process Intensification: Profits for
the Chemical Industry; Rotterdam, May, 1998.
(
(
1
(
(24) Noguchi, T.; Hiraia, Y.; Kirihara, M. Chem. Commun. 2008,
P.; Avinigiri, M. L.; Chalamala, S.; Sundaram, V.; Mathad, V. T.;
Bhattacharya, A.; Bandichhor, R. Tetrahedron Lett. 2007, 48, 8001.
3
040.
(
b) Elati, R. C.; Kolla, N.; Vankawala, J. P.; Gangula, S.; Chalamala, S.;
Sundaram, V.; Bhattacharya, A.; Vurimidi, H.; Thippannachar, V. M.
Org. Process Res. Dev. 2007, 11, 289.
(
7) Taghavi- Moghadam, S.; Kleemann, A.; Golbig, K. G. Org. Process
Res. Dev. 2001, 5, 652.
8) Schwalbe, T.; Autze, V.; Hohmann, M.; Stirner, W. Org. Process
Res. Dev. 2004, 8, 440.
9) (a) Laia, M. S.; Flavien, S. J. Med. Chem. 2012, 55, 4062.
b) Jachuck, R. J.; Ramshaw, C.; Boodhoo, K.; Dalgleish, J. C. Inst.
(
(
(
Chem. Eng. Symp. Ser. 1997, 141, 417. (c) Anderson, N. G. Practical
Process Research and Development: A Guide for Organic Chemists, 2nd
ed.; Academic Press: New York, 2012. (d) Rode, C. V.; Ghalwadkar, A.
A.; Mane, R. B.; Hengne, A. M.; Jadkar, S. T.; Biradar, N. S. Org.
Process Res. Dev. 2010, 14, 1385.
(
10) (a) Fell, N.; Ramshaw, C. Chem. Eng. 1998, 656, 23.
(
b) Brocklehurst, C. E.; Lehmann, H.; Vecchia, La. L. Org. Process
Res. Dev. 2011, 15, 1447. (c) Roydhouse, M. D.; Ghaini, A.;
Constantinou, A.; Cantu-Perez, A.; Motherwell, W. B.; Gavriilidis, A.
Org. Process Res. Dev. 2011, 15, 989.
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dx.doi.org/10.1021/op300325f | Org. Process Res. Dev. XXXX, XXX, XXX−XXX