2-Nitrotoluene → HCID 12906240, compound

HRID 1579543Notes

Reaction equation

HRID 1579543 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH3:10])([O-:3])=[O:2].C(O[CH:14](OCC)[N:15]([CH3:17])[CH3:16])C>CN(C)C=O>[CH3:14][N:15]([CH3:17])/[CH:16]=[CH:10]/[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 69442-NitrotolueneHCID 70913Dimethylformamide diethylacetal

Product 1

HCID 12906240HCID 12906240, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 34.3 g. of 2-nitrotoluene in a mixture of 37 g. of N,N-dimethylformamide diethylacetal and 100 ml. of dimethylformamide was heated under reflux for 26 hours. The dark reaction mixture was concentrated by first removing the lower boiling components on a rotary evaporator and then distilling the unreacted 2-nitrotoluene at about 75°/0.2 mm. The residual dark, red liquid (35 g., 72%), which was trans-β-dimethylamino-2-nitrostyrene, was used directly in the experiments below without further purification.

Workup

  1. temperatureunder reflux for 26 hours
  2. customThe dark reaction mixture
  3. concentrationwas concentrated
  4. customby first removing the
  5. customon a rotary evaporator
  6. distillationdistilling the unreacted 2-nitrotoluene at about 75°/0.2 mm
  7. customwas used directly in the experiments below without further purification

Sources & evidence

ORD record
ord-f3e4a11c432c4b6eba2cfbbf12e47c72
Source dataset
uspto-grants-1976_01
Patent number
US03931225

Reaction notes

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