Benzoic acid, 4-aMino-5-cyano-2-hydroxy-3-Methyl-, ethyl ester synthesis
- Product Name:Benzoic acid, 4-aMino-5-cyano-2-hydroxy-3-Methyl-, ethyl ester
- CAS Number:72817-85-7
- Molecular formula:C11H12N2O3
- Molecular Weight:220.22
Yield:72817-85-7 59%
Reaction Conditions:
Stage #1: ethyl propanoylacetatewith sodium ethanolate in ethanol at 0 - 20;
Stage #2: Ethoxymethylenemalononitrile in ethanol at 20 - 80; for 2 h;
Stage #3: with hydrogenchloride;water in ethanol; pH=7;
Steps:
74
Example 74 4-Amino-5-cyano-2-hydroxy-3-methylbenzoic acid ethyl ester (74) To a solution of sodium ethoxide (1.3 L) (freshly prepared by addition of sodium metal (7.9 g, 0.35 mol) to ethanol (1.3 L)) at 0° C. was added ethylpropionyl acetate (25 g, 0.17 mol) and the solution was stirred at RT for 1 h. To the above solution was added ethoxymethylene malonormitrile (21 g, 0.17 mol) at RT and the reaction mixture was refluxed at 80° C. for 2 h. The reaction mixture was cooled, neutralized to pH=7 by addition of 1.5 N HCl and concentrated under vacuum. The obtained residue was diluted with water (100 mL) and filtered. The solid was washed with water and dried under vacuum at 50° C. to give the crude product (27 g). The crude solid was washed with 5% ethyl acetate in pet. ether which gave pure title compound (22.5 g, 59%).
References:
US2009/118312,2009,A1 Location in patent:Page/Page column 52
123-06-8
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