Reaction #1458444

ord-7ecc4fa55db949479212a9302120d7ca

Reaction equation

CC(C(=O)O)c1ccc(NC(=O)c2ccccc2O)cc1
2-(4-(N-salicyloyl)aminophenyl-)propionic acid
CCO
ethanol
[Na+].[OH-]
NaOH
→
CC(C(=O)[O-])c1ccc(NC(=O)c2ccccc2O)cc1.[Na+]
sodium 2-(4-(N-salicyloyl)aminophenyl)propionate
Yield 92.1%

Reactants

CC(C(=O)O)c1ccc(NC(=O)c2ccccc2O)cc1
2-(4-(N-salicyloyl)aminophenyl-)propionic acid
CCO
ethanol
[Na+].[OH-]
NaOH

Reagents

None

Solvents

O
water

Conditions

Temperature
0°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThe resulting pale yellow solid is isolated by filtration

Procedure

A solution of 53.05 g (0.186 mol) of 2-(4-(N-salicyloyl)aminophenyl-)propionic acid and 300 ml of ethanol is treated with 7.59 g (0.190 mol) of NaOH dissolved in 22 ml of water. The reaction mixture is stirred for 30 min at 25° C. and for 30 min at 0° C. The resulting pale yellow solid is isolated by filtration to give 52.61 g of sodium 2-(4-(N-salicyloyl)aminophenyl)propionate. Properties. Solubility: 200 mg/ml clear solution, pH=6.85. Analysis C, 60.45; H, 5.45; N, 3.92; Na, 6.43. Melting point 236–238° C.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07157426B2uspto-grants-2007_01