7-Amino-3,4-dihydro-1H-quinolin-2-one

A suspension of Pd(OH)(b) 7-Amino-3, 4-dihydroquinolin-2(1H)-one. To a solution of methyl-3-(2, 4-dinitrophenyl)acrylate from step (a) above (4.3 g, 117 mmol) in EtOH (75 mL) and acetic acid (8 mL) was added 10% Pd/C (1.4 g) and the mixture was shaken under hydrogen atmosphere (60 psi) on a Parr shaker for 6 h. The catalyst was filtered through a Celite pad and the filter cake was washed with EtOH (2×35 mL). The combined filtrates were concentrated and the residue dried under vacuo to give the title compound as a yellowish-brown solid. MS (ESI, pos. ion.) m/z: 163 (M+1).(b) 7-Amino-1, 3, 4-trihydroquinolin-2-one. Ethyl 3-(2, 4-dinitrophenyl)prop-2-enoate, Example 22(a), (3.0 g, 11 mmol) was dissolved in glacial acetic acid (240 mL), treated with 10% Pd on carbon (2.4 g, Aldrich) and hydrogenated on a Parr shaker apparatus at 65 C., under 60 psi H2, for 3 h. The reaction mixture was allowed to cool to 25 C., purged with N2, filtered through Celite and the filtercake washed with acetic acid (200 mL) and EtOH (200 mL). The combined filtrate was concentrated in vacuo, then treated with 1 N NaOH (150 mL) and extracted with EtOAc (3*100 mL). The combined organic extract was washed with satd NaCl (50 mL), dried over Na2SO4, filtered and concentrated in vacuo. Purification by silica gel chromatography (EtOAc) provided the title product as a pale yellow solid. MS (ESI, pos. ion) m/z: 163 (M+1).To a solution of General procedure: Thionyl chloride (1.6g, 13mmol) was added to a mixture of 13a (597mg, 2.0mmol), DCE (10mL), and 3 drops of DMF under cooling in an ice-water bath, and the solution was stirred for 2h at room temperature. The reaction solution was concentrated under reduced pressure. DCE (20mL), 6-amino-1, 3-dihydro-2H-indol-2-one (269mg, 1.82mmol), and triethylamine (726mg, 7.17mmol) were added to the residue, and the mixture was stirred at room temperature for 12h. Water was added to the reaction mixture and the aqueous phase was extracted with CHCl3. The combined organic phase was washed with water, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (CHCl3/MeOH/28% aqueous NH3) to obtain a light yellow solid, which was dissolved in EtOH/EtOAc and a 4M hydrogen chloride solution in EtOAc was added. The solvent was removed by evaporation and the residue was triturated with EtOH to give 20 as a pale pink powder (273mg, 32% yield).

Molecular Weight:162.19
XLogP3:0.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Exact Mass:162.079312947
Monoisotopic Mass:162.079312947
Topological Polar Surface Area:55.1
Heavy Atom Count:12
Complexity:193
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes