反応 #220856

反応方程式

indole-3-pyruvic acid

hydroxylamine hydrochloride salt

sodium pyruvate

4-hydroxy-4-(3-indolylmethyl)-2-ketoglutaric acid

sodium hydroxide

hydrochloric acid

sodium hydroxide

→

4-hydroxy-4-(3-indolylmethyl)-2-hydroxyiminoglutaric acid

収率 32.0%

溶媒

sodium carbonate

反応条件

後処理

1. 1
   その他was obtained
2. 2
   抽出to extract the organic matter in ethyl acetate
3. 3
   洗浄The organic layer was rinsed with aqueous saturated sodium chloride
4. 4
   乾燥dried over anhydrous magnesium sulfate
5. 5
   濃縮subsequently concentrated
6. 6
   その他to obtain the residue
7. 7
   その他The residue was recrystallized in aqueous 28% ammonia and ethanol

実験手順

After 10.0 g (49.2 mmol) of indole-3-pyruvic acid was added to and dissolved in 98 ml of aqueous saturated sodium carbonate solution, the resulting solution was adjusted to pH 12.4 using aqueous 25% sodium hydroxide solution. After 16.3 g (147.6 mmol) of sodium pyruvate was added for reaction at ambient temperature for 2 hours, a reaction solution containing 4-hydroxy-4-(3-indolylmethyl)-2-ketoglutaric acid was obtained. 13.7 g (197 mmol) of hydroxylamine hydrochloride salt was added to the reaction solution while the reaction solution was adjusted to a pH value around neutrality using aqueous 25% sodium hydroxide solution, and agitated at ambient temperature for 4 hours. Using conc. hydrochloric acid, the reaction solution was adjusted to an acidic pH value, to extract the organic matter in ethyl acetate. The organic layer was rinsed with aqueous saturated sodium chloride, dried over anhydrous magnesium sulfate and subsequently concentrated, to obtain the residue. The residue was recrystallized in aqueous 28% ammonia and ethanol, to obtain 5.51 g of 4-hydroxy-4-(3-indolylmethyl)-2-hydroxyiminoglutaric acid (16.2 mmol; a yield of 32% vs. indole-3-pyruvic acid) in crystal form.

出典