6-Bromo-N-methyl-2-naphthalenecarboxamide

Reference Example 76-Bromo-2-naphthoic acid (10.1 g, 40.1 mmol) and N, N- dimethylformamide (4.75 g, 65.0 mmol) were added to toluene (80 mL) . To the reaction mixture was added dropwise thionyl chloride (5.7 g, 48.2 mmol) at 45 to 50°C, and the mixture was stirred for 1 hr, and allowed to cool to room temperature. The reaction mixture was added dropwise at 10 to 25°C to a solution prepared by adding triethylamine (11.4 g, 112.4 mmol) and 40percent methylamine methanol solution (8.1 g, 104.4 mmol) to toluene (80 rnL) , and the mixture was stirred at room temperature for 1 hr.. To the reaction mixture was added dropwise water (50 mL) , and the mixture was stirred at room temperature. The crystals were collected by filtration, and washed with a mixed solvent (25 mL) of methanol/water (2:8) to give wet crystals. The total amount of the wet crystals was added to N, N- dimethylacetamide (70 mL) , and dissolved with heating to 60°C. The reaction mixture was allowed to cool to room temperature, and water (140 mL) was added dropwise thereto. The crystals were collected by filtration, and washed with water (80 mL) to give wet crystals. The total amount of the wet crystals was suspended in ethyl acetate -(25 mL) with stirring at roomtemperature. The crystals were collected by filtration, and washed with ethyl acetate (5 mL) . The obtained wet crystals were dried under reduced pressure to give 6-bromo-N-methyl-2- naphthamide (9.4 g, 35.6 mmol). yield 89percent.3/4 NMR (500 MHz, DMSO-dUnder an argon atmosphere, to a cooled (0 °C) solution of 8 (60.26 g, 240 mmol), EDCI*HCl (55.21 g, 288 mmol), HOBt*H4 Liters of ethyl acetate and 25 ML of DMF were added to 500 g (1.99 mol) of 6-bromo-2-naphthoic acid. 188 ML (2.61 mol, 1.3eq) of thionyl chloride was added dropwise at 30°C or lower..

Molecular Weight:264.12
XLogP3:3.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:262.99458
Monoisotopic Mass:262.99458
Topological Polar Surface Area:29.1
Heavy Atom Count:15
Complexity:244
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes