Acetic Acid → 2-Amino-5-(methoxycarbonyl)benzoic acid

HRID 2110035

Reaktionsgleichung

[NH2:1][C:2]1[CH:10]=[CH:9][C:8](I)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].CCN(CC)CC.[CH:19]1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C]=O.[C:50]([OH:53])(=[O:52])C>CN(C=O)C.CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([C:50]([O:53][CH3:19])=[O:52])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

After dissolving 2-amino-5-iodobenzoic acid (4 mmol, 1052 mg) in DMF (10 ml) and MeOH (5 ml), NEt3 (3 eq, 1.67 ml) was added. Next, palladium acetate (0.1 eq, 90 mg) and dppp (0.1 eq, 165 mg) were added, carbon monoxide substitution was carried out, and the mixture was stirred at 80° C. for 5 hours. Upon completion of the reaction, acetic acid (2.5 ml) was added to suspend the reaction. Water (50 ml) was added, and extraction was performed with ethyl acetate (50 ml×3 times). The organic layer was washed with water (100 ml×2 times) and then dried over sodium sulfate. After concentration, a developing solvent (Hex/AcOEt=4/1→1/1) was used for purification by silica gel chromatography to obtain 2-amino-5-(methoxycarbonyl)benzoic acid. The compound was identified by LC-MS.

Aufarbeitung

additionwas added
additionwas added
customthe reaction
extractionextraction
washThe organic layer was washed with water (100 ml×2 times)
dry with materialdried over sodium sulfate
concentrationAfter concentration
customa developing solvent (Hex/AcOEt=4/1→1/1) was used for purification by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag: ord-048688c5d3694dddb090ba85c4bb8d4f
Quelldatensatz: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07517875B2

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