4-AMINO-2-IODOBENZONITRILE98

Off-white crystalline

To a solution of 4-aminobenzonitrile (2.4 g 20 mmol) and -30percent HINTERMEDIATE 56 - PREPARATION of 4-Amino-3-iodobenzonitrile. Iodine (0.645 g; 2.54 mmol) was added to a stirred mixture of silver sulphate (0.791 g;2.54 mmol) and 4-aminobenzonitrile (0.300 g; 2.54 mmol) in ethanol (10 ml_). The reaction mixture was then stirred at room temperature for 18 hours and filtered over celite. The volatiles were removed under reduced pressure and the residue was partitioned between ethyl acetate and a saturated aqueous solution of sodium thiosulfate. The organic layer was washed with brine, dried and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (eluent 2 to 40 percent ethyl acetate in heptane) to afford 0.222 g (36percent) of the title compound as a white solid.1 H NMR (DMSO-de) δ 7.96 (d, 1 H), 7.45 (dd, 1 H), 6.76 (d, 1 H), 6.22 (s, 2H).Iodine (0.645 g; 2.54 mmol) was added to a stirred mixture of silver sulphate (0.791 g; 2.54 mmol) and 4-aminobenzonitrile (0.300 g; 2.54 mmol) in ethanol (10 mL). The reaction mixture was then stirred at room temperature for 18 hours and filtered over celite. The volatiles were removed under reduced pressure and the residue was partitioned between ethyl acetate and a saturated aqueous solution of sodium thiosulfate. The organic layer was washed with brine, dried and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (eluent 2 to 40percent ethyl acetate in heptane) to afford 0.222 g (36percent) of the title compound as a white solid. [0654] INTERMEDIATE 142 - PREPARATION of 4-amino-3-iodobenzonitrile; Iodine (0.645 g; 2.54 mmol) was added to a stirred mixture of silver sulphate (0.791 g; 2.54 mmol) and 4-aminobenzonitrile (0.300 g; 2.54 mmol) in ethanol (10 ml_). The reaction mixture was stirred at room temperature for 18 hours and filtered over celite. The volatiles were removed under reduced pressure and the residue was partitioned between ethyl acetate and a saturated aqueous solution of sodium thiosulphate.. The organic layer was washed with brine, dried and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (eluent 2 to 40 percent ethyl acetate in heptane) to afford 0.222 g (36percent) of the title compound as a white solid. 1H NMR (DMSO-de) δ 7.96 (d, 1 H), 7.45 (dd, 1 H), 6.76 (d, 1 H), 6.22 (s, 2H).EXAMPLE 10 Step 1 : Preparation of 4-amino-3-iodobenzonitrile To a solution of 4-aminobenzonitrile (10 g) in DMA (50 mL) was added N- iodosuccinamide (19.80 g).The reaction mixture was stirred at 45-50°C for 72 h. The reaction mass was quenched in water and obtained solid was filtered to afford 10 g of title product.To a solution of 4-aminobenzonitrile (10 g) in DMA (50 mL) was added N-iodosuccinamide (19.80 g).The reaction mixture was stirred at 45-50°C for 72 h. The reaction mass wasquenched in water and obtained solid was filtered to afford 10 g of title product.

Palladium-catalyzed carbonylation of iodoanilines provides ketoamides in the presence of primary and secondary amines.8

Molecular Weight:244.03
XLogP3:1.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:243.94975
Monoisotopic Mass:243.94975
Topological Polar Surface Area:49.8
Heavy Atom Count:10
Complexity:160
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes