Nitromethane → 2-Methoxy-1-(2-nitroethenyl)naphthalene

HRID 1451543Notes

Reaction equation

HRID 1451543 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[CH:13]=O.C([O-])(=O)C.[NH4+].[N+:20]([CH3:23])([O-:22])=[O:21]>O>[N+:20]([CH:23]=[CH:13][C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:11]=[CH:12][C:3]=1[O:2][CH3:1])([O-:22])=[O:21]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 793522-Methoxy-1-naphthaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 8966262-Methoxy-1-(2-nitroethenyl)naphthaleneYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.52 g of 2-methoxynaphthaldehyde (8.16 mmol), 0.4 g of ammonium acetate (5.19 mmol) and 20 cm3 of nitromethane (96%) are introduced into a 50-cm3 two-necked round-bottomed flask equipped with a condenser. The reaction mixture is heated to reflux for 1 h 30 min while stirring. It becomes yellow. The nitromethane is evaporated off in a rotary evaporator and the residue is then taken up with dichloromethane. Hydrolysis of the ammonium acetate is carried out by pouring the above mixture into water. The aqueous phase is washed twice with CH2Cl2, the organic phase once with water. The latter phase is dried with MgSO4 and the solvent is removed in a rotary evaporator. 1.77 g of yellow crystals (equivalent to 7.73 mmol of the expected product) are then obtained, corresponding to a 95% yield.

Workup

  1. customequipped with a condenser
  2. temperatureThe reaction mixture is heated
  3. temperatureto reflux for 1 h 30 min
  4. customThe nitromethane is evaporated off in a rotary evaporator
  5. customHydrolysis of the ammonium acetate
  6. washThe aqueous phase is washed twice with CH2Cl2
  7. dry with materialThe latter phase is dried with MgSO4
  8. customthe solvent is removed in a rotary evaporator

Sources & evidence

ORD record
ord-2179ab30ce444f43af1d0b35bcea43ef
Source dataset
uspto-grants-1997_02
Patent number
US05604261

Reaction notes

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