Received 28 August 2012
The title compound, C11H11NO2, was synthesized by chemoselective N-acetylation of 4-aminophenol followed by reaction with propargyl bromide in the presence of K2CO3. the acetamide and propyn-1-yloxy substituents form dihedral angles of 18.31 (6) and 7.01 (10)°, respectively, with the benzene ring. In the crystal, molecules are linked by N-HO hydrogen bonds into chains along . C-HO and C-H interactions also occur.
For background to the development of hybrid drug candidates against tuberculosis, malaria and cancer, see: Morphy et al. (2004). For details of the synthesis of the title compound, see: Hoogendoorn et al. (2011); Reppe (1955).
Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT and XPREP (Bruker, 2008); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 1999).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2291 ).
Research funds of the University of Johannesburg and the Research Centre for Synthesis and Catalysis are gratefully acknowledged. Mrs Z. H. Phasha is thanked for the data collection.
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Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.
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Hoogendoorn, S., Blom, A. E. M., Willems, L. I., van der Marel, G. A. & Overkleeft, H. S. (2011). Org. Lett. 13, 5656-5659.
Morphy, R., Kay, C. & Rankovic, Z. (2004). Drug Discov. Today, 9, 641-651.
Reppe, W. (1955). Justus Liebigs Ann. Chem. 596, 38-79.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.