2-amino-6-nitro-phenol

To a nitrogen flushed solution of 2, 6-dinitrophenol (10 g, 54.3 mmol) in ethyl acetate (100 ml) was added 10percent palladium on carbon (0.5 g) and the resulting mixture stirred under a balloon of hydrogen for 5 hours. The catalyst was removed by filtration and the filtrate evaporated to give the title compound (8.0 g, 95percent). 1H NMR (400 MHz, CDC13) 8 3.95 (2H, br s), 6.78 (1H, t, J 8. 4 and 8.0), 6.95 (1H, dd, J7. 6 and 1.2), 7.46 (1H, DD, J 8. 6 AND 1.2).To a of solution of 2, 6-dinitrophenol (5.43 mmol, 1.00 g) in methanol (100 mL), 10percent palladium on activated carbon (10 wtpercent of 2, 6-dinitrophenol, 0.10 g) was added. The reaction was flushed with argon followed by hydrogen for fifteen minutes each with constant magnetic stirring. The reaction was then maintained under hydrogen atmosphere at ordinary pressure (balloon) for one hour. The reaction was monitored closely by thin layer chromatography to avoid over reduction.1 Argon was again flushed through the reaction vessel for 15 minutes. Then the reaction contents were filtered over a thin pad of celite which was then washed with methanol (50 mL). The filtrate was concentrated in vacuo yielding a brown solid. Silica gel column chromatography (10:1 hexanes/ethyl acetate) provided a crystalline red solid in a 92percent yield.2-Amino-6-nitrophenol: A suspension of 2, 6-dinitrophenol 5.0 g (27 mmol), ammonium hydroxide (3 ml) and ammonium chloridel4. 3 g (270 mmol) in 30 ml of water was heated to 70°C. A solution of sodium sulfide nonahydrate (24.19 g, 100 mmol) in water was added and the resulting mixture stirred at 70°C for 2h. The reaction was cooled to room temperature, acidified (pH 3.2) with 2N HC1, and the brown precipitate separated by filtration. The filtrate was extracted with chloroform (6 x 75 ml), the organic extracts combined with the precipitate, and evaporated in-vacuo to yield 2.5 g (60 percent) of product as a dark brown solid. 1H NMR (CDC13) 5 4.09 (s, 2H), 6.78 (t, 1H, J = 8. 2 Hz), 6.95 (d, 1H, J = 7.8 Hz), 7.47 (d, 1H, J = 8.6 Hz), 10.73 (s, 3H).Step 1 (1) To a nitrogen flushed solution of 2, 6-dinitrophenol (10 g, 54.3 mmol) in ethyl acetate (100 ml) was added 10percent palladium on carbon (0.5 g) and the resulting mixture stirred under a balloon of hydrogen for 5 hours. The catalyst was removed by filtration and the filtrate evaporated to give the title compound (8.0 g, 95percent). 1H NMR (400 MHz, CDC13) 8 3.95 (2H, br s), 6.78 (1H, t, J 8. 4 and 8.0), 6.95 (1H, dd, J7. 6 and 1.2), 7.46 (1H, DD, J 8. 6 AND 1.2).To a of solution of 2, 6-dinitrophenol (5.43 mmol, 1.00 g) in methanol (100 mL), 10percent palladium on activated carbon (10 wtpercent of 2, 6-dinitrophenol, 0.10 g) was added. The reaction was flushed with argon followed by hydrogen for fifteen minutes each with constant magnetic stirring. The reaction was then maintained under hydrogen atmosphere at ordinary pressure (balloon) for one hour. The reaction was monitored closely by thin layer chromatography to avoid over reduction.1 Argon was again flushed through the reaction vessel for 15 minutes. Then the reaction contents were filtered over a thin pad of celite which was then washed with methanol (50 mL). The filtrate was concentrated in vacuo yielding a brown solid. Silica gel column chromatography (10:1 hexanes/ethyl acetate) provided a crystalline red solid in a 92percent yield.2-Amino-6-nitrophenol: A suspension of 2, 6-dinitrophenol 5.0 g (27 mmol), ammonium hydroxide (3 ml) and ammonium chloridel4. 3 g (270 mmol) in 30 ml of water was heated to 70°C. A solution of sodium sulfide nonahydrate (24.19 g, 100 mmol) in water was added and the resulting mixture stirred at 70°C for 2h. The reaction was cooled to room temperature, acidified (pH 3.2) with 2N HC1, and the brown precipitate separated by filtration. The filtrate was extracted with chloroform (6 x 75 ml), the organic extracts combined with the precipitate, and evaporated in-vacuo to yield 2.5 g (60 percent) of product as a dark brown solid. 1H NMR (CDC13) 5 4.09 (s, 2H), 6.78 (t, 1H, J = 8. 2 Hz), 6.95 (d, 1H, J = 7.8 Hz), 7.47 (d, 1H, J = 8.6 Hz), 10.73 (s, 3H).Step 1 (1)

Molecular Weight:154.12
XLogP3:1.6
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Exact Mass:154.03784206
Monoisotopic Mass:154.03784206
Topological Polar Surface Area:92.1
Heavy Atom Count:11
Complexity:156
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes