Facile Decarboxylation of Nitrobenzeneacetic Acids as a Convenient Route to Alkylnitrobenzenes

Synlett

Volumn 1996, Issue 7, 1996, Pages 647-648

  Bull, David J ^a   Fray, M Jonathan ^a   Mackenny, Malcolm C ^a   Malloy, Kerry A ^a  

^a PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003164340     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5561     Document Type: Article

References (16)

1. For reviews of the VNS reaction see Makosza, M.; Winiarski, J., Acc. Chem. Res. 1987, 20, 282; Makosza, M., Synthesis, 1991, 103.
2. For reviews of the VNS reaction see Makosza, M.; Winiarski, J., Acc. Chem. Res. 1987, 20, 282; Makosza, M., Synthesis, 1991, 103.
3. Mudryk, B.; Makosza, M., Synthesis, 1988, 1007.
4. Margerum, D. J.; Petrusis, C. T., J. Am. Chem. Soc. 1969, 91, 2467
5. Toussaint, O.; Capdevielle, P.; Maumy, M., Tetrahedron, 1984, 40, 3229.
6. Nagarajan, K.; Rao, V. R.; Shah R. K.; Shenoy, S. J.; Fritz, H.; Richter, W. J.; Muller, D., Helv. Chim. Acta. 1988, 71, 77.
7. 3a has previously been prepared in 4 steps, 19% overall yield. Eur. Patent. 385,850 A2 (Chem. Abstr. 1991, 114, P 81830t).
8. 3a has previously been prepared in 4 steps, 19% overall yield. Eur. Patent. 385,850 A2 (Chem. Abstr. 1991, 114, P 81830t).
9. Nitroarenes can be alkylated by treatment with alkyllithiums followed by oxidation, see Kienzle, F., Helv. Chim. Acta. 1978, 61, 449. For reviews on nucleophilic addition to electron-deficient arenes, see Bartoli, G., Acc. Chem. Res. 1984, 17, 109; Paradisi, C. in Comprehensive Organic Synthesis: selectivity, strategy and efficiency in modern organic chemistry, editor Barry M. Trost, Pergamon Press, Oxford, 1991, vol. 4, 423.
10. Nitroarenes can be alkylated by treatment with alkyllithiums followed by oxidation, see Kienzle, F., Helv. Chim. Acta. 1978, 61, 449. For reviews on nucleophilic addition to electron-deficient arenes, see Bartoli, G., Acc. Chem. Res. 1984, 17, 109; Paradisi, C. in Comprehensive Organic Synthesis: selectivity, strategy and efficiency in modern organic chemistry, editor Barry M. Trost, Pergamon Press, Oxford, 1991, vol. 4, 423.
11. Nitroarenes can be alkylated by treatment with alkyllithiums followed by oxidation, see Kienzle, F., Helv. Chim. Acta. 1978, 61, 449. For reviews on nucleophilic addition to electron-deficient arenes, see Bartoli, G., Acc. Chem. Res. 1984, 17, 109; Paradisi, C. in Comprehensive Organic Synthesis: selectivity, strategy and efficiency in modern organic chemistry, editor Barry M. Trost, Pergamon Press, Oxford, 1991, vol. 4, 423.
12. 4), evaporated in vacua and the residue purified by flash chromatography on silica to give 1.
13. Standard procedure for the hydrolysis: A stirred solution of 1 (13 mmoles) in dioxane (50 mL) was treated with aqueous sodium hydroxide (15.6 mL, 1molar solution) for 3 hours at room temperature. The solution was concentrated under reduced pressure, the solid dissolved in water (200 mL) and acidified to pH2 with hydrochloric acid (2M). The precipitated solid was collected by filtration and dried to give 2.
14. α-Branching can also be achieved by alkylation of the VNS products derived from ethyl chloroacetate. Makosza, M.; Wrobel, Z., Heterocycles, 1992, 33, 585; Lawrence, N. J.; Liddle, J., Synlett, 1996, 55.
15. α-Branching can also be achieved by alkylation of the VNS products derived from ethyl chloroacetate. Makosza, M.; Wrobel, Z., Heterocycles, 1992, 33, 585; Lawrence, N. J.; Liddle, J., Synlett, 1996, 55.
16. 4), evaporated in vacua and the residue purified by flash chromatography on silica to give 3.