تفاعل #1605779

معادلة التفاعل

2-(5-methylpyridin-2-yl)ethanamine

(2-methoxy-4-methylphenyl)methanamine hydrochloride salt

triethylamine

ethyl 2-chloro-2-oxoacetate

→

N1-(2-methoxy-4-methylbenzyl)-N2-(2-(5-methylpyridin-2-yl)ethyl) oxalamide

المردود 30.0%

المذيبات

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONAfter the addition
2. 2
   درجة الحرارةThe reaction was heated
3. 3
   درجة الحرارةat reflux for 24 hours
4. 4
   أخرىAfter removal of the solvent
5. 5
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate
6. 6
   غسيلwashed successively with water and brine
7. 7
   تجفيفdried over MgSO4
8. 8
   ترشيحfiltered
9. 9
   أخرىevaporated
10. 10
    غسيلThe residue was washed with methyl t-butyl ether (20 mL)
11. 11
    أخرىrecrystallized from ethanol

الإجراء التجريبي

To a mixture of 1.8 g of (2-methoxy-4-methylphenyl)methanamine hydrochloride salt and triethylamine (5.1 mL, 3 equiv.) in dry acetonitrile (45 mL) was added ethyl 2-chloro-2-oxoacetate (1.47 mL, 1 equiv.) dropwise at 0° C. under nitrogen atmosphere. After the addition was complete, the reaction mixture was stirred at room temperature for 2 hours and 2-(5-methylpyridin-2-yl)ethanamine (2.52 g, 1.4 equiv.) was added. The reaction was heated at reflux for 24 hours. After removal of the solvent, the residue was dissolved in ethyl acetate and washed successively with water and brine, dried over MgSO4, filtered, and evaporated. The residue was washed with methyl t-butyl ether (20 mL) and recrystallized from ethanol to give 1.3 g of N1-(2-methoxy-4-methylbenzyl)-N2-(2-(5-methylpyridin-2-yl)ethyl) oxalamide as a white powder (yield 30%).

المصدر