2-(3-Aminophenyl)ethanol

In tetrahydrofuran (2 mL) solution of 2-(3-nitrophenyl) ethanol (200 mg, 1.20 mmol), 10percent palladium carbon (M) Dry (20 mg) was added under ice-cooling and argon gas atmosphere. Hydrogen gas replaced, after degassing the inside of a reaction container under decompression. Reaction mixture was violently stirred for 90 minutes under a room temperature and hydrogen gas atmosphere (balloon). After washing the insoluble matter by filtration and THF and being crowded, concentration hardening by drying was doubled and carried out, and the filtrate and the washing liquid obtained the compound (an opalescence solid, 165 mg, and 1.20 mmol, quantitive) of the mark.Step A: (28A) A mixture of nitro phenethyl alcohol (8.Og, 0.047mol) and 10percent Pd/C (0.6g) in ethanol (100ml) was stirred under a hydrogen atmosphere (balloon pressure) for 18 h. The reaction mixture was filtered through a pad of celite and the Pd/C catalyst removed. The filtrate was concentrated under reduced pressure to yield a light brown solid 6.1 g (95percent yield). LCMS purity 98percent, m/z 138 [M+H]3-Nitrophenethyl alcohol (4.8g, 28. 7mmol) was dissolved in 117ml ethyl acetate. A small amount of 5percent palladium on activated carbon was added. The reaction was stirred overnight at room temperature under hydrogen atmosphere. According to thin layer chromatography all the starting material was consumed. The mixture was filtered through CELITE and the solvent was evaporated to give 3.7g (93percent yield) of the desired product. 1HNMR (400MHZ, CDC13) : 2.76 (t, 2H), 3.81 (t, 2H), 6.52-6. 57 (M, 2H), 6.62 (d, 1H), 7.06- 7.11 (M, 1H)Into a 250-mi. round-bottom flask, was placed a solution of 2-(3-nitrophenyl)ethan-1-olg, 6.58 mmol, 1.00 equiv) in ethanol (100 mL). 10percent Palladium on carbon (500 mg) wasadded to the reaction mixture. The resulting solution was stirred overnight at room temperature under hydrogen atmosphere. The solids were filtered out. The filtrate was concentrated under vacuum to yield 800 mg (89percent) of 2-(3-aminophenyl)ethan-1-ol as a brown oil.Into a 250-mL round-bottom flask, was placed a solution of 2-(3-nitrophenyl)ethan-l-ol (1.1 g, 6.58 mmol, 1.00 equiv) in ethanol (100 mL). 10percent Palladium on carbon (500 mg) was added to the reaction mixture. The resulting solution was stirred overnight at room temperature under hydrogen atmosphere. The solids were filtered out. The filtrate was concentrated under vacuum to yield 800 mg (89percent) of 2-(3-aminophenyl)ethan-l-ol as a brown oil.Example 129 2, 4-DIMETHYL-N- (4- ((1 R, 2S)-2- [4- (2-METHYL-5-QUINOLINYL)-1- PIPERAZINYL] CYCLOPROPYL} PHENYL)-1, 3-THIAZOLE-5-CARBOXAMIDE DIHYDROCHLORIDE and 2, 4-DIMETHYL-N-(4-{(1 R, 2S)-2- [4- (2-METHYL-5-QUINOLINYL)-1- PIPERAZINYL] CYCLOPROPYL} PHENYL)-1, 3-THIAZOLE-5-CARBOXAMIDE DIHYDROCHLORIDE (E129) 2- (3-Aminophenyl) ethanol; 2- (3-Nitrophenyl) ethanol (836mg, 5. 00mmol) and Pd (10percent on charcoal, 200mg) were suspended in dry methanol (10 mL). After the addition of ammonium formate (1.450g, 23MMOL) a slightly exothermic and effervescent reaction was observed. After stirring for 1h at room temperature the mixture was filtered over celite. The filtrate was evaporated and the residue dissolved in ethyl acetate. After washing with saturated aqueous sodium hydrogencarboante solution, water and brine the organic layer was dried (magnesium sulfate) and the solvent removed under reduced pressure affording the title compound in 54percent yield (373mg) as a white solid. MS; (ES) m/z: 138 [MH+]. CGHNNO requires 137. 1H-NMR (300 MHz, d6-DMSO) B (ppm): 6.80 (t, 1H), 6.25-6. 35 (m, 3H), 4.85 (s, 2H), 4.50 (t, 1 H), 3.45 (dt, 2H), 2.45 (t, 2H).

Molecular Weight:137.18
XLogP3:0.6
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:137.084063974
Monoisotopic Mass:137.084063974
Topological Polar Surface Area:46.2
Heavy Atom Count:10
Complexity:95.3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes