Ethanol → 3-Nitro-2-vinylaniline

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-])=O)[C:5]=1[CH:13]=[CH2:14])([O-:3])=[O:2].C(O)C.O.O.O.O.O.O.O.O.O.[S-2].[Na+].[Na+]>O>[N+:1]([C:4]1[C:5]([CH:13]=[CH2:14])=[C:6]([CH:7]=[CH:8][CH:9]=1)[NH2:10])([O-:3])=[O:2]

Participants

Procedure

The product from Example 44A (0.669 g, 3.45 mmoles) in 3:1 ethanol:water (40 mL) was treated with sodium sulfide nonahydrate (1.66 g, 6.90 mmoles) and heated at reflux for 30 minutes. The mixture was allowed to cool to room temperature and then concentrated under reduced pressure. The residue was mixed with water and extracted with chloroform (2×). The chloroform extracts were combined, washed with brine, dried with sodium sulfate and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, 25% ethyl acetate/hexanes) to provide the title compound (0.137 g, 24%). MS (DCI) m/z 165 (M+H)+.