HCID 16412775, Verbindung → 2-Methyl-1,3-benzoxazol-4-amine
Reaktionsgleichung
[CH3:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-])=O)[C:5]=2[N:6]=1>C(O)(=O)C.C(OCC)(=O)C.[Fe]>[NH2:11][C:7]1[C:5]2[N:6]=[C:2]([CH3:1])[O:3][C:4]=2[CH:10]=[CH:9][CH:8]=1Komponenten
4
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 65 °C
Versuchsvorschrift
Compound 474A (6.78 g, 38.1 mmol) was dissolved in a 1:1 mixture of 10% acetic acid/ethyl acetate (100 mL total volume) and heated to 65° C. Iron powder (10.63 g, 190.2 mmol) was added portionwise. After stirring for 3 h, TLC indicated complete consumption of starting material. The cooled reaction mixture was filtered through a pad of Celite and the pad was washed with 50 mL of ethyl acetate. The organic layer was separated, washed with water (2×25 mL), brine (1×25 mL), dried over MgSO4, filtered and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel eluting with 25% ether/CH2Cl2 to give 3.90 g (69%) of compound 474B as a light brown solid. HPLC: 95.8% at 2.43 min (retention time) (YMC S5 ODS column, 4.6×50 mm, eluting with 10-90% aqueous methanol over 4 min containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm). MS (ES): m/z 149.11 [M+H]+.