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

HRID 479017

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:12])[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.C[Si](Cl)(C)C.C(N(CC)CC)C.CC([O:28][C:29]1[C:34]([C:35](Cl)=[O:36])=[CH:33][CH:32]=[CH:31][CH:30]=1)=O>C(Cl)Cl>[C:35]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH3:12])[C:9]([OH:11])=[O:10])=[CH:6][CH:7]=1)(=[O:36])[C:34]1[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=1)[OH:28]

Participants

Conditions

Temperature: 0 °C

Procedure

A slurry of 58.6 g (0.355 mol) of 2-(4-aminophenyl)propionicacid and 500 ml of methylene chloride was treated with 90.11 ml (77.13 g, 0-710 mol) of trimethylsilyl chloride and was heated to reflux for 120 min. The reaction mixture was 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 was treated with a solution of 70.45 g (0.355 mol) of O-acetylsalicyloyl chloride and 150 ml of methylene chloride. The reaction mixture was warmed to 25° C. and stirred for 64 hr. The volatiles were removed in vacuo. The residue was stirred in 2N aqueous sodium hydroxide for one hour and acidified with 2 M aqueous sulfuric acid. The solid was recrystallized twice from ethanol/water to give a tan solid. Isolation by filtration afforded 53.05 g of (52% yield) of 2-(4-(N-salicyloyl)aminophenyl)propionic acid.

Workup

temperaturewas heated
temperatureto reflux for 120 min
temperatureThe reaction mixture was warmed to 25° C.
stirringstirred for 64 hr
customThe volatiles were removed in vacuo
stirringThe residue was stirred in 2N aqueous sodium hydroxide for one hour
customThe solid was recrystallized twice from ethanol/water
customto give a tan solid
filtrationIsolation by filtration

Sources & evidence

ORD record: ord-1ae6f0b86b0f4478bba672050e38a6c8
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06642411B1

Linked notes

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