تفاعل #164932

معادلة التفاعل

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

المردود 99.9%

المذيبات

1,4-dioxane

ظروف التفاعل

المعالجة

1. 1
   أخرىThe reaction mixture was flushed with N2
2. 2
   درجة الحرارةAfter cooling to room temperature
3. 3
   workup.ADDITIONthe mixture was diluted with H2O
4. 4
   استخلاصextracted with ethyl acetate
5. 5
   غسيلThe combined organic layer was washed with brine
6. 6
   تجفيفdried over Na2SO4
7. 7
   تركيزconcentrated under reduced pressure
8. 8
   أخرىThe residue was purified by flash chromatography

الإجراء التجريبي

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.

المصدر