Tetrahydrofuran → 4-Amino-2-iodobenzonitrile

A mixture of compound 489B (4.60 g, 16.8 mmol), tetrahydrofuran (75 mL), ethanol (100 mL), ammonium chloride solution (1.51 g, 28.3 mmol, dissolved in 100 mL of water), and iron (325 mesh, 4.21 g, 75.4 mmol) was mechanically stirred. The reaction mixture was heated to reflux for 3 h or until all starting material was consumed. The reaction mixture was cooled, filtered through Celite and concentrated in vacuo. The resulting residue was dissolved in ethyl acetate (200 mL) and washed with 1N sodium hydroxide (2×150 mL), dried over sodium sulfate, filtered and concentrated in vacuo to yield 3.97 g (97%) of compound 489C as a dark solid. HPLC: 95% at 1.877 min (retention lime) (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 245.13 [M+H]+.

1. temperatureThe reaction mixture was heated
2. temperatureto reflux for 3 h or until all starting material
3. customwas consumed
4. temperatureThe reaction mixture was cooled
5. filtrationfiltered through Celite
6. concentrationconcentrated in vacuo
7. dissolutionThe resulting residue was dissolved in ethyl acetate (200 mL)
8. washwashed with 1N sodium hydroxide (2×150 mL)
9. dry with materialdried over sodium sulfate
10. filtrationfiltered
11. concentrationconcentrated in vacuo

ORD-Eintrag

ord-fcd1a7698ce34de4872f35068173f966

Quelldatensatz

uspto-grants-2005_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06953679B2