Réaction #1742640

Équation de réaction

methyl 3-aminobenzoate

triethylamine

valeryl chloride

→

prisms

Rendement 87.0%

Methyl 3-valerylaminobenzoate

Rendement 87.0%

Solvants

methylene chloride

Conditions de réaction

Traitement

1. 1
   Températurecooling
2. 2
   workup.STIRRINGThe mixture was stirred for one hour
3. 3
   LavageThe reaction mixture was washed with an aqueous solution of sodium bicarbonate, dilute hydrochloric acid and water
4. 4
   Autreby drying
5. 5
   Concentrationconcentration to dryness
6. 6
   AutreThe concentrate was crystallized from ethyl acetate-hexane

Mode opératoire

To a solution of methyl 3-aminobenzoate (6.0 g) and triethylamine (4.5 g) in methylene chloride (90 ml) was added dropwise, while stirring under ice-cooling, valeryl chloride (4.8 g). The mixture was stirred for one hour. The reaction mixture was washed with an aqueous solution of sodium bicarbonate, dilute hydrochloric acid and water, followed by drying and concentration to dryness. The concentrate was crystallized from ethyl acetate-hexane to afford colorless prisms (8.1 g, 87%), m.p. 101-102° C. 1H-NMR(90 MHz, CDCl3) δ: 0.93(3H,t), 1.2-1.9(4H,m), 2.37(2H,t), 3.90(3H,s), 7.36(1H,t), 7.5(1H,br s), 7.70-7.95(2H,m), 8.03(1H,t).

Source