(E)-Methyl 2-(2-(((1,3-dioxoisoindolin-2-yl) oxy)methyl)phenyl)-2-(methoxyimino)aceta te synthesis
- Product Name:(E)-Methyl 2-(2-(((1,3-dioxoisoindolin-2-yl) oxy)methyl)phenyl)-2-(methoxyimino)aceta te
- CAS Number:156581-14-5
- Molecular formula:C19H16N2O6
- Molecular Weight:368.35
Yield:156581-14-5 98%
Reaction Conditions:
with sodium hydroxide;nitrogen in N-methyl-acetamide;water;
Steps:
2 Preparation of methyl (E)-2-(aminooxymethyl)phenyl glyoxylate O-methyloxime Methyl (E)-2-(O-phthalimidoxymethyl)phenyl glyoxylate O-methyloxime
To a dry 500 ml round bottom flask equipped with magnetic stirrer, and nitrogen inlet was charged 5.1 g (0.0315 moles) of N-hydroxyphthalimide, 1.3 g (0.0315 moles) of sodium hydroxide, and 300 ml of anhydrous dimethylformamide. The dark red solution was stirred at ambient temperature for 20 min., followed by the addition of the methyl 2-(bromomethyl)phenylglyoxylate O-methyloxime (15 g, 60% pure, 0.0315 moles) in one portion. The reaction was stirred at ambient temperature over the weekend, then poured into 800 mls of water and stirred for 1 hour to afford a white solid which was collected by vacuum filtration and washed with water, hexane, and dried under vacuum at 40° C. overnight. Isolated 11.5 g of a white solid (98% isolated yield) which was consistent with the desired product, methyl (E)-2-(O-phthalimidoxymethyl)phenyl glyoxylate O-methyloxime, upon analysis by 300 MHz 1 H NMR. NMR (300 MHz, 1 H, CDCl3, TMS=0 ppm) 3.8 (s, 3H), 3.95 (s, 3H), 5.0 (s, 2H), 7.1 (d, 1H), 7.5 (m, 2H), 7.7-7.9 (m, 5H).
References:
US6063956,2000,A
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