Reaction #1458443

Reaction equation

2-(4-aminophenyl)propionic acid

trimethylsilyl chloride

O-acetylsalicyloyl chloride

triethylamine

→

2-(4-(N-salicyloyl)aminophenyl)propionic acid

Yield 52.4%

Solvents

methylene chloride

methylene chloride

Conditions

Workup

1. 1
   Temperatureis heated
2. 2
   Temperatureto reflux for 120 min
3. 3
   TemperatureThe reaction mixture is warmed to 25° C.
4. 4
   workup.STIRRINGstirred for 64 hr
5. 5
   OtherThe volatiles are removed in vacuo
6. 6
   workup.STIRRINGThe residue is stirred in 2N aqueous sodium hydroxide for one hour
7. 7
   OtherThe solid is recrystallized twice from ethanol/water
8. 8
   Otherto give a tan solid
9. 9
   FiltrationIsolation by filtration

Procedure

A slurry of 58.6 g (0.355 mol) of 2-(4-aminophenyl)propionic acid and 500 ml of methylene chloride is treated with 90.11 ml (77.13 g. 0–710 mol) of trimethylsilyl chloride and is heated to reflux for 120 min. The reaction mixture is cooled to 0° C. and treated with 184.44 ml (107.77 g, 1.065 mol) of triethylamine. After stirring for 5 minutes, this mixture is treated with a solution of 70.45 g (0.355 mol) of O-acetylsalicyloyl chloride and 150 ml of methylene chloride. The reaction mixture is warmed to 25° C. and stirred for 64 hr. The volatiles are removed in vacuo. The residue is stirred in 2N aqueous sodium hydroxide for one hour and acidified with 2 M aqueous sulfuric acid. The solid is recrystallized twice from ethanol/water to give a tan solid. Isolation by filtration results in an expected yield of 53.05 g (52% yield) of 2-(4-(N-salicyloyl)aminophenyl)propionic acid. Properties. Solubility: 200 mg/m: 200 mg+350.μL 2N NaOH+650.μL H2O-pH-7.67. Analysis: C, 67.36; H, 5.3; N, 4.91.

Source