6-Aminophthalide

white to light yellow crystal powde

Commercially available 6-nitro-1(3H)-isobenzofuranone (9.9 g, 55 mmol) was dissolved in a mixed solvent of tetrahydrofuran (20 ml)-methanol (60 ml), then 5percent palladium-charcoal catalyst (1.5 g) was added thereto, and the mixture was stirred at room temperature for 20 hours under an atmosphere of hydrogen gas. The reaction mixture was filtered, and the solid was washed successively with ethyl acetate and methanol. The filtrate and washings were combined, and the resulting solution was concentrated under reduced pressure. The obtained solid was washed with ethyl acetate to give the title compound (6.21 g) as a crystalline solid. The washings were concentrated, and the residue was crystallized from a mixed solvent of ethyl acetate-hexane to give an additional amount of the title compound (0.95 g, total yield 87percent). NMR spectrum (400 MHz, CD3OD) δ ppm: 5.225 (2H, s), 7.060 (1H, d-like, J=2 Hz), 7.071 (1H, dd-like, J=9, 2 Hz), 7.288 (1H, d, J=9 Hz) IR spectrum ν max KBr cm-1: 3473, 3372, 3278, 1735, 1631, 1504, 1330, 1059, 992.6-Nitro-3H-isobenzofuran-1-one 1)> (2.00 g, 11.1 mmol) was dissolved in methanol (25 ml), and 20percent palladium/ carbon (200 mg) was added thereto, followed by stirring at room temperature for 12 hours in the presence of hydrogen gas (50 psi). The reaction solution was filtered and concentrated under reduced pressure to obtain the title compound (1.43 g, 86percent). [1326] 1H NMR (400 MHz, DMSO-dStep b: To a solution of 6-nitroisobenzofuran-1(3H)-one (15 g, 0.080 mol) in HCl/H2O (375 mL/125 mL) was added SnCl2.2H2O (75 g, 0.33 mol). General procedure: To a screw top vial (5 mL) under N2 containing freshly distilled toluene (0.6 mL) were successively added an aromatic nitro compound (0.60 mmol), InI3 (14.9 mg, 0.030 mmol), and TMDS (318 μL, 1.80 mmol). After the vial was sealed with a cap that contained a PTFE septum, the mixture was stirred at 60 °C (bath temperature), and monitored via TLC analysis. Sat. aq NaHCO3 solution (5 mL) was added to the resultant mixture, which was then extracted with EtOAc (3 × 6 mL). The combined organic phases were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (n-hexane–EtOAc, 9:1 to 4:1) to afford the corresponding aniline derivative.

Molecular Weight:149.15
XLogP3:0.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:149.047678466
Monoisotopic Mass:149.047678466
Topological Polar Surface Area:52.3
Heavy Atom Count:11
Complexity:181
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes