Реакция #8877

Уравнение реакции

3-dimethylamino-1-(2,4-dichlorophenyl)-2-(4-chlorophenyl)prop-2-en-1-one

cyanoacetamide

methanol

sodium hydride

→

6-(2,4-Dichlorophenyl)-5-(4-chlorophenyl)-2-oxo-1,2-dihydropyridine-3-nitrile

Растворители

DMF

DMF

Условия реакции

Обработка

1. 1
   workup.ADDITIONAfter the slow addition
2. 2
   ДругоеMost of the DMF was then removed in vacuo before the reaction
3. 3
   workup.ADDITIONwas diluted with aqueous 18% citric acid solution
4. 4
   ЭкстракцияThe mixture was extracted twice with methylene chloride
5. 5
   Промывкаthe organic layers were washed with a portion of brine
6. 6
   СушкаThe combined organic layers were dried over anhydrous sodium sulfate
7. 7
   Концентрированиеconcentrated in vacuo
8. 8
   ДругоеThe solid residue was triturated with ether
9. 9
   Фильтрацияfiltered
10. 10
    Другоеair dried
11. 11
    Другоеto afford the product

Методика

A solution of 3-dimethylamino-1-(2,4-dichlorophenyl)-2-(4-chlorophenyl)prop-2-en-1-one (14.4 mmol assumed) from Step A, cyanoacetamide (1.33 g, 15.8 mmol), and methanol (1.3 mL, 32 mmol) in DMF (35 mL) was added dropwise to a suspension of sodium hydride (60% in mineral oil) (1.45 g, 36 mmol) in DMF (16 mL) at rt. After the slow addition was complete, the reaction was heated to 95° C. for 2.5 h. Most of the DMF was then removed in vacuo before the reaction was diluted with aqueous 18% citric acid solution. The mixture was extracted twice with methylene chloride and the organic layers were washed with a portion of brine. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. The solid residue was triturated with ether, filtered, and air dried to afford the product. HPLC/MS: 375 (M+1), 377 (M+3); Rt=3.47 min; 1H NMR (CDCl3): δ 6.96 (br d, J=8.4 Hz,2H), 7.14 (d, J=8.2 Hz, 1H), 7.25 (br d, J=8.4 Hz, 2H), 7.31 (dd, J=1.9 and 8.2 Hz, 1H), 7.50 (d, J=2.0 Hz, 1H), 7.996 (s, 1H).

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