Реакция #214542

Уравнение реакции

pivaloyloxymethyl 2-chloro-3-pyridinecarboxylate

3-chloro-2-methylaniline

hydrochloric acid

→

Pivaloyloxymethyl 2-(2'-methyl-3'-chloro-anilino)-3-pyridinecarboxylate

Условия реакции

Обработка

1. 1
   workup.ADDITIONare charged
2. 2
   Другоеthe reaction the mixture
3. 3
   ДругоеDuring the reaction the temperature of the reaction mixture
4. 4
   Другоеrises to 190° C
5. 5
   ДругоеWhen reaction
6. 6
   ТемператураThe reaction mixture is then cooled to room temperature
7. 7
   ДругоеThe solid is separated by filtration
8. 8
   Промывкаthe cake washed with water
9. 9
   workup.DISSOLUTIONThen the washed solid is dissolved in hot methanol
10. 10
    Другоеrecrystallized
11. 11
    Температураby cooling the methanolic solution
12. 12
    ДругоеThe crystallized product is separated
13. 13
    Другоеdried under vacuum, at a temperature of 40° C

Методика

Into a suitable flask, pivaloyloxymethyl 2-chloro-3-pyridinecarboxylate prepared according to Example 2, supra (21.7 g) and 3-chloro-2-methylaniline (28.4 g) are charged. To begin the reaction the mixture is heated to 140° C. During the reaction the temperature of the reaction mixture rises to 190° C. When reaction is completed, the temperature diminishes. The reaction mixture is then cooled to room temperature. Diluted hydrochloric acid is added to the cooled mixture and the precipitated compound ground into small particles and suspended in the reaction mixture. The solid is separated by filtration and the cake washed with water. Then the washed solid is dissolved in hot methanol and recrystallized by cooling the methanolic solution. The crystallized product is separated and dried under vacuum, at a temperature of 40° C. Pivaloyloxymethyl 2-(2'-methyl-3'-chloro-anilino)-3-pyridinecarboxylate (m.p. 90°-91° C.) is so obtained, with a yield of 22.5 g (77.6% of theory).

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