Pyridine → Methyl 2-hydroxy-3-(3-methylbenzamido)benzoate
Reaktionsgleichung
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH2:10])[C:5]=1[OH:11].N1C=CC=CC=1.[CH3:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[C:23](Cl)=[O:24]>C1(C)C=CC=CC=1>[OH:11][C:5]1[C:6]([NH:10][C:23](=[O:24])[C:22]2[CH:26]=[CH:27][CH:28]=[C:20]([CH3:19])[CH:21]=2)=[CH:7][CH:8]=[CH:9][C:4]=1[C:3]([O:2][CH3:1])=[O:12]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
Thionyl chloride (30 mL) was added to 1 (4.5 g, 33 mmol) and the mixture was stirred at reflux overnight. Thionyl chloride was evaporated under reduced pressure and the residue was dried in vacuum to obtain 3-methylbenzoyl chloride (3.59 g). Methyl-3-amino-2-hydroxybenzoate (3.34 g, 20.0 mmol) and pyridine (2 mL) were added to toluene (10 mL) and the mixture was stirred at room temperature for 30 min. Then 3-methylbenzoyl chloride (1.54 g, 10 mmol) was added. The mixture was stirred at room temperature for 30 min and then at 80° C. for 2 hr. The resulting mixture was extracted with ethyl acetate (100 mL×4) and concentrated. The crude product was purified by column chromatography (silica gel, petroleum ether:ethyl acetate 20:1 to 5:1) to obtain methyl 2-hydroxy-3-(3-methylbenzamido)benzoate as a solid (1.8 g, yield 63%). LC-MS (ESI) m/z 287 [M+1]+.
Aufarbeitung
- stirringThe mixture was stirred at room temperature for 30 min
- waitat 80° C. for 2 hr
- extractionThe resulting mixture was extracted with ethyl acetate (100 mL×4)
- concentrationconcentrated
- customThe crude product was purified by column chromatography (silica gel, petroleum ether:ethyl acetate 20:1 to 5:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-7b51d8db20374f2d9ace04e574d4c534
- Quelldatensatz
- uspto-grants-2012_01
- Patentnummer
- US08088760B2
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