Ammonia → 2-Hydroxy-1-naphthamide

A solution of 2-hydroxy-1-napthoic acid (5.0 g, 26.6 mmol), 1-(3-dimethylaminopropyl) 3-ethylcarbodiimide hydrochloride (5.6 g, 29.2 mmol), and 1-hydroxybenzotriazole (3.95 g, 29.2 mmol) in tetrahydrofuran (70 ml) was stirred at room temperature for 30 minutes prior to the addition of 0.880 NH3 (6 ml). The resulting suspension was stirred at room temperature for 2 hours. The reaction mixture was filtered and the filtrate diluted with water (80 ml) and extracted with ethyl acetate (4×80 ml). The combined organic extracts were washed with water (50 ml×2), saturated aqueous sodium chloride (50 ml), dried (sodium sulfate) and the solvent removed in vacuo to give an orange oil. Purification by column chromatography on silica gel eluting with dichloromethane:methanol:0.880 ammonia 95:5:0.5 gave the title compound as a pink solid (1.83 g).

1. filtrationThe reaction mixture was filtered
2. additionthe filtrate diluted with water (80 ml)
3. extractionextracted with ethyl acetate (4×80 ml)
4. washThe combined organic extracts were washed with water (50 ml×2), saturated aqueous sodium chloride (50 ml)
5. dry with materialdried (sodium sulfate)
6. customthe solvent removed in vacuo
7. customto give an orange oil
8. customPurification by column chromatography on silica gel eluting with dichloromethane

ORD record

ord-149df5bf1bab46d8891f8841e09333b5

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07767715B2