2-(5-Hydroxybenzo[d]isoxazol-3-yl)acetic Acid synthesis
- Product Name:2-(5-Hydroxybenzo[d]isoxazol-3-yl)acetic Acid
- CAS Number:34173-03-0
- Molecular formula:C9H7NO4
- Molecular Weight:193.16
Yield:34173-03-0 54%
Reaction Conditions:
with hydroxylamine hydrochloride in ethanol;sodium hydrogencarbonate;
Steps:
1.A Step A
Step A A suspension of 4,6-dihydroxycoumarin (0.5 g) in absolute ethanol (15 cm3), containing hydroxylamine hydrochloride (0.58 g) and sodium metal (0.2 g), was heated at reflux for 9 hours. A grey precipitate formed during this period. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure and the residue dissolved in aqueous sodium bicarbonate solution. The aqueous solution was extracted with diethyl ether. The ether extract was dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to give a solid (0.09 g), 2,5-dihydroxyacetophenone oxime by NMR. The aqueous solution was acidified with concentrated hydrochloric acid and then extracted with diethyl ether. The ether extract was dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to give a yellow-orange solid, 5-hydroxy-1,2-benzoxazol-3-ylacetic acid (0.29 g, 54%), m.p. 170° C. (decomposition). δH (CDCl3) 3.95(s)2H; 7.00(d)1H; 7.05(dd)1H; 7.50(d)1H; 9.60(broad s)1H; 12.80(broad s)1H.
References:
US5176737,1993,A
30992-75-7
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