2-amino-3-chlorophenol

To a solution of 3-chloro-2-nitrophenol (2.5g, 14.Smmol) in EtOH (3OmL) was added SnCl2.2H20 (13g, 57.8mmol) at rt. The reaction mixture was stirred at 90 00 for 2h. The TLC showed reaction to be complete. The reaction mixture was cooled to rt and concentrated under reduced pressure. The ice —water (5OmL) was added to residue and basified to pH 7 with aq NH3 solution. The mixture was extracted with EtOAc (3x 5OmL). The organic layer was washed with brine (5OmL), dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was triturated with hexane (25mL) to afford 2-amino-3-chlorophenol as an off white solid. Yield: 1.8 g (80percent); 1H NMR (400 MHz, DMSO-d6): 9.58 (bs, 1H), 6.69 (d, J= 8.0 Hz, 1H), 6.63 (d, J= 8.0 Hz, 1H), 6.38-6.48 (m, 1H), 4.05 (bs, 2H); MS (ESl+) for CHNOS m/z 144.09 [M+H].Step 2:The crude aminophenol 10b (6.37 g, 36.7 mmol) is dissolved in THF (100 mL) and tin powder (17.4 g, 147 mmol) is added followed by 1 N HCI (220 mL, 220 mmol). The resulting mixture is stirred vigorously at RT. After 16 h, the reaction is cooled to OThe crude aminophenol 10b (6.37 g. 36.7 mmol) is dissolved in THF (100 mL) and tin powder (17.4 g, 147 mmol) is added followed by 1 N HCI (220 mL, 220 mmol). The resulting mixture is stirred vigorously at RT. After 16 h, the reaction is cooled to OThe crude aminophenol 10b (6 37 g 36 7 mmol) is dissolved in THF (100 mL) and tin powder (17 4 g, 147 mmol) is added followed by 1 N HCI (220 mL, 220 mmol) The resulting mixture is stirred vigorously at RT After 16 h, the reaction is cooled to OThe crude aminophenol 10b (6.37 g, 36.7 mmol) is dissolved in THF (100 mL) and tin powder (17.4 g, 147 mmol) is added followed by 1 N HCI (220 mL, 220 mmol). The resulting mixture is stirred vigorously at RT. After 16 h, the reaction is cooled to OStep A: A mixture of 3-chloro-2-nitrophenol (18.95 g, 100 mmol) and Pd/C (10percent, 0.50 g) in MeOH (300 mL) was stirred under HStep A: To a cooled (0 To a stirred solution of

Molecular Weight:143.57
XLogP3:1.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Exact Mass:143.0137915
Monoisotopic Mass:143.0137915
Topological Polar Surface Area:46.2
Heavy Atom Count:9
Complexity:99.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes