3-aMino-2-naphthaMide

B. 2-Aminonaphthalene-3-Carboxamide Ammonia is intermittently bubbled into a suspension of benzoisatoic anhydride (5.0 g., 2.25 millimoles) and ethanol (80 ml.) for a period of two days. The bright green solid which formed is filtered from the reaction mixture, dried and then recrystallized from ethanol. Yield = 1.95 g. (46%) of the title amide. M.P. 234-235C. (m/e - 186).General procedure: To a solution of 5-hexynoic acid (3.0 mmol) in dryCH2Cl2 (5 mL) was added EDCI (3.1 mmol) and HOBt(3.1 mmol). The resulting mixture was stirred at rt for 2 h. Then substituted or unsubstituted 2-aminobenzamide (3.0 mmol) wasadded, and the reaction mixture was stirred at rt for 12 h whilebeing monitored by TLC. After the addition of H2O (10 mL) themixture was extracted with ethyl acetate (3 × 20 mL). Theorganic layers were combined and concentrated under vacuumto give the amide intermediate.General procedure: To a solution of 5-hexynoic acid (3.0 mmol) in dryCH2Cl2 (5 mL) was added EDCI (3.1 mmol) and HOBt(3.1 mmol). The resulting mixture was stirred at rt for 2 h. Then substituted or unsubstituted 2-aminobenzamide (3.0 mmol) wasadded, and the reaction mixture was stirred at rt for 12 h whilebeing monitored by TLC. After the addition of H2O (10 mL) themixture was extracted with ethyl acetate (3 × 20 mL). Theorganic layers were combined and concentrated under vacuumto give the amide intermediate.General Protocol I: Synthesis of o-amino carboxamides:; To a solution of the 2-amino benzoic acid in THF was slowly added phosgene as a 20% solution in toluene (1.1 equivalents). The resulting suspension was allowed to stir at room temperature until solids had completely dissolved, and then cooled to O0C. The flask was fitted with an addition funnel and ammonium hydroxide was cautiously added as a 27% aqueous solution (10 equivalents). After one hour the organic phase was diluted with ethyl acetate, washed twice with aqueous sodium bicarbonate and saturated aqueous sodium chloride, and dried over sodium sulfate. Filtration and removal of the residual solvent gave the desired amides as white solids with sufficient purity for use in subsequent chemical transformations.; Intermediate A1 :

Molecular Weight:186.21
XLogP3:1.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:186.079312947
Monoisotopic Mass:186.079312947
Topological Polar Surface Area:69.1
Heavy Atom Count:14
Complexity:229
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes