2-Amino-4-(trifluoromethyl)phenol

2-Amino-4-(trifluoromethyl)phenol. (D7); A solution of 2-nitro-4-(trifluoromethyl)phenol (100 mg, 0.483 mmol) in ethanol (10 ml.) was pumped through an H-cube.(TM). hydrogenator CatCart (Pd/C, 30 x 4 mm) at a flow rate of 1 mL/min at 40 A solution of 2-nitro-4-(trifluoromethyl)phenol (100 mg, 0.483 mmol) in ethanol (10 mL) was pumped through an H-cube.(TM). hydrogenator CatCart (Pd/C, 30 x 4 mm) at a flow rate of 1 mL/min at 40 0860] 2-Nitro-4-trifluoromethylphenol (340 μL, 2.41 mmol) was dissolved in methanol (50 mL) and processed through the H-Cube with a 10percent Pd/C Catalyst cartridge at ambient temperature and pressure. The eluent was concentrated under reduced pressure to provide 2-amino-4-trifluoromethylphenol as a light brown solid (438 mg, 100percent). (CI, m/z): [M+H]To a suspension of palladium hydroxide (3.05 g, 21.7 mmol) in methanol was added a methanol solution of 2-nitro-4-(trifluoromethyl)phenol (1.00 g, 4.8 mmol) followed by solid ammonium formate (3.04 g, 48.3 mmol). The mixture was heated at 85° C. and monitored by TLC. The completed reaction was allowed to cool to rt and was filtered through a pad of Celite.(R)., washing with ethyl acetate. The filtrate was concentrated under reduced pressure to provide the title compound (0.58 g, 67percent). LC-MS m/z 178.1 (MH+), retention time 0.55 minutes.mixture of compound 21 (0.500 g), ammonium formate (0.761 g), 10percent Pd / C (0.050 g) and methanol (12 mL) was stirred at 50 ° C. for 1 hour.The reaction mixture was filtered through celite, concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate solution was added to the residue, and the mixture was extracted with ethyl acetate.The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain compound 22 (0.410 g).11.4 g of potassium carbonate was added to 48.7 g of 7B in 320 ml of acetone. Then 18.2 of ethyl 2, 3-dibromopropionate was added dropwise to the refluxing mixture. This procedure was repeated thrice. The mixture was refluxed for 17 hours and filtered, and the filtrate was stripped of solvent under reduced pressure. The residue was dissolved in ether; the solution was washed with dilute sodium hydroxide solution, then dried (MgSO4) and stripped of solvent. The residue was washed with petroleum ether and dried. The residue was mixed with ether and filtered. Part of the solvent was evaporated from the filtrate; the remaining solution was cooled. Crystals which formed were filtered and recrystallized from ether to give 7, m.p.: 105-107.General procedure: Example 3 General procedure for preparation of amino compound Experimental procedure C A suspension of nitro compound and Pd-C ( 10%) in EtOAc/MeOH was stirred under hydrogen atmosphere (1 - 2 atm). After completion of reaction, the reaction mixture was filtered and concentrated under reduced pressure. The resulting crude was purified by silica gel (100-200) chromatography to produce the requisite aromatic amino compounds as shown in scheme 5. 2.1 l-aminonaphthalen-2-ol (AP01): The general experimental procedure C was followed. Yellow solid. M. P.: 235.8 C; IR (CHC13): v 3385, 3313, 1633, 1604, 1573, 1508, 1463, 1376, 1336, 1274, 1072, 859 cm-1; NMR (CDC13, 200 MHz): delta 2.33 (s, 6H), 7.21 (s, IH), 7.48 (s, 2H), 7.70 (s, IH), 7.73 (d, J = 8.8 Hz, IH), 9.07 (d, J = 8.8 Hz, IH), 9.64 (s, IH), 10.73 (s, IH), 13.25 (s, IH) ppm; i3C NMR (CDC13, 50 MHz): delta 1 16.9 (d), 119.1 (d), 1 19.6 (d), 122.3 (d), 124.5 (d), 124.8 (s), 125.8 (s), 127.7 (d), 128.5 (s), 140.2 (s) ppm; ESI-MS (m/z): 181. 1 [M+Na]+; Anal. Calcd for Ci0H9NO: C, 75.45; H, 5.70; N, 8.80; Found: C, 75.50; H, 5.75; N, 8.85.

Molecular Weight:177.12
XLogP3:1.7
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Exact Mass:177.04014830
Monoisotopic Mass:177.04014830
Topological Polar Surface Area:46.2
Heavy Atom Count:12
Complexity:159
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes