5-Methoxy-2-nitrobenzeneacetic acid

General procedure: 1 equivalent of nitrile was dissolved in a mixture of AcOH/HCl (1:5) andrefluxed for 4 h. The product was extracted with ethyl acetate, dried over Na(Intermediate 6), 1.54 g (36, 8 mmoi) of lithium hydroxide monohydrate, 90 mL of THF and 45 mL of water was stirred at room temperature for 16 hours. The organic solvent was evaporated and the residue was extracted with ethyl acetate. 40 mL of 1 A/ hydrochloric acid was added to the aqueous phase, extracted twice with ethyl acetate, the combined organic phases were dried over anhydrous Na2S04, filtered and concentrated. Thus, 2.27 g (35%) of the title product was obtained. MS (ESI) m/z 229.1 (M+NH4)+.To a mixture of 2.27 g (10.7 mmol) of (5-methoxy-2-nitrophenyl) acetic acid (Intermediate 7), 40 mL of dry acetonitrile, 1.70 g (11.8 mmol) of Meldrum's acid, 131 mg (1.07 mmol) of DMAP and 4.21 mL (24.2 mmol) of DIPEA, 1.46 mL (11.8 mmol) trimethyiacetyi chloride was added dropwise and the reaction mixture was stirred at 40C for 4 hours. The mixture was cooled to OX, 26 mL of 1 N hydrochloric acid was added dropwise and diluted with 60 mL of water. The precipitated product was filtered off, washed with water and dried over phosphorus pentoxide in a vacuum desiccator. Thus, 2.45 g (68%) of the title product was obtained which was used without further purification.

Molecular Weight:211.17
XLogP3:1.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:3
Exact Mass:211.04807239
Monoisotopic Mass:211.04807239
Topological Polar Surface Area:92.4
Heavy Atom Count:15
Complexity:249
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes