反応 #164932

反応方程式

1,10-phenanthroline

K3PO4

2-Hydroxy-4-methylpyridine

3-iodo-5-nitro-benzoic acid methyl ester

2-Hydroxy-4-methylpyridine

3-Iodo-5-nitro-benzoic acid methyl ester

→

3-(4-Methyl-2-oxo-2H-pyridin-1-yl)-5-nitro-benzoic acid methyl ester

収率 99.9%

溶媒

1,4-dioxane

反応条件

後処理

1. 1
   その他The reaction mixture was flushed with N2
2. 2
   温度After cooling to room temperature
3. 3
   workup.ADDITIONthe mixture was diluted with H2O
4. 4
   抽出extracted with ethyl acetate
5. 5
   洗浄The combined organic layer was washed with brine
6. 6
   乾燥dried over Na2SO4
7. 7
   濃縮concentrated under reduced pressure
8. 8
   その他The residue was purified by flash chromatography

実験手順

To a 25 ml round-bottomed flask was added 2-Hydroxy-4-methylpyridine (17.9 mg, 0.164 mmol), 3-Iodo-5-nitro-benzoic acid methyl ester (40 mg, 0.137 mmol), CuI (5.2 mg, 0.027 mmol) and 1,4-dioxane (10 ml). The reaction mixture was stirred for 5 minutes to the dissolve 2-Hydroxy-4-methylpyridine and 3-iodo-5-nitro-benzoic acid methyl ester, after which 1,10-phenanthroline (9.84 mg, 0.055 mmol) was added, followed by K3PO4 (174 mg, 0.082 mmol). The reaction mixture was flushed with N2, and heated to 110° C. for 24 hours. After cooling to room temperature, the mixture was diluted with H2O, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by flash chromatography to give 3-(4-Methyl-2-oxo-2H-pyridin-1-yl)-5-nitro-benzoic acid methyl ester (39.45 mg, 61%) as light yellow solid. MS (M+H)=289.

出典