Ethanol → 3-Nitro-2-vinylaniline

HRID 1370809Notes

Reaction equation

HRID 1370809 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

5

Reactant 3

HCID 702EthanolHCID 73972Sodium sulfide nonahydrateHCID 107264561,3-Dinitro-2-vinylbenzene

Product 1

HCID 185122573-Nitro-2-vinylanilineYield 24.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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)+.

Workup

  1. temperatureheated
  2. temperatureat reflux for 30 minutes
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue was mixed with water
  5. extractionextracted with chloroform (2×)
  6. washwashed with brine
  7. dry with materialdried with sodium sulfate
  8. concentrationthe filtrate concentrated under reduced pressure
  9. customThe residue was purified by flash chromatography (silica gel, 25% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-3e36d8a1a58e4a4c802fd28b58d3b4d4
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

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