Nitromethane → HCID 15057534, compound

HRID 1463376Notes

Reaction equation

HRID 1463376 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH2:11][C:10](=O)[CH2:9][CH2:8]2.[N+:14]([CH3:17])([O-:16])=[O:15]>C(N)CN>[CH3:1][O:2][C:3]1[C:12]2[CH:11]=[C:10]([CH2:17][N+:14]([O-:16])=[O:15])[CH2:9][CH2:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 6375NitromethaneHCID 41360218-Methoxy-2-tetralone

Product 1

HCID 15057534HCID 15057534, compound

Reagents, catalysts & solvents 1

HCID 3301EthylenediamineSolvent

Procedure

44.1 g of 8-methoxy-2-tetralone (0.25 mol) are stirred at 70° C. under argon for 3 h in 402 ml of nitromethane (7.50 mol) and 2.5 ml of ethylenediamine. After the mixture has cooled to room temperature, a yellow crystallisate is filtered off with suction. The nitromethane is distilled off from the solution in vacuo. The residue is dissolved in 500 ml of toluene. The solvent is again distilled off in vacuo in order to remove nitromethane residues. The residue is then dissolved in 200 ml of toluene again. An insoluble component is filtered off and the solution is concentrated to 50 ml. The concentrated solution is then chromatographed on 500 g of silica gel using toluene. After concentrating the main fraction, the final product is obtained as a yellow oil.

Workup

  1. filtrationa yellow crystallisate is filtered off with suction
  2. distillationThe nitromethane is distilled off from the solution in vacuo
  3. dissolutionThe residue is dissolved in 500 ml of toluene
  4. distillationThe solvent is again distilled off in vacuo in order
  5. customto remove nitromethane residues
  6. dissolutionThe residue is then dissolved in 200 ml of toluene again
  7. filtrationAn insoluble component is filtered off
  8. concentrationthe solution is concentrated to 50 ml
  9. customThe concentrated solution is then chromatographed on 500 g of silica gel
  10. concentrationAfter concentrating the main fraction

Sources & evidence

ORD record
ord-5368c686e8ab4a149884750d2ef7209d
Source dataset
uspto-grants-1994_04
Patent number
US05300523

Reaction notes

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