Ethanol → sodium 2-(4-(N-salicyloyl)aminophenyl)propionate

HRID 456375Notes

Reaction equation

[C:1]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([CH3:21])[C:18]([OH:20])=[O:19])=[CH:13][CH:12]=1)(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].C(O)C.[OH-].[Na+:26]>O>[C:1]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([CH3:21])[C:18]([O-:20])=[O:19])=[CH:13][CH:12]=1)(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[Na+:26]

Participants

Conditions

Temperature: 0 °C

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.

Workup

customThe resulting pale yellow solid is isolated by filtration

Sources & evidence

ORD record: ord-77f14a7c3825410b87a38dcdac7f5be5
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07186691B2

Reaction notes

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