2,6-Dinitrotoluene → N,N-Dimethyl-2-phenylethen-1-amine

HRID 1684819Notes

Reaction equation

HRID 1684819 reaction equation
[N+]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+]([O-])=O)[C:5]=1[CH3:13])([O-])=O.CO[CH:16](OC)[N:17]([CH3:19])[CH3:18]>CN(C=O)C>[CH3:16][N:17]([CH:19]=[CH:13][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:4]=1)[CH3:18]

Participants

4

Reactant 2

HCID 118132,6-DinitrotolueneHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 23277871N,N-Dimethyl-2-phenylethen-1-amineYield 139.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture solution of 2,6-dinitrotoluene (18.2 g, 0.1 mol) and N,N-dimethylformamide dimethylacetal (28 mL, d=0.89, 0.2 mol) in anhydrous DMF (80 mL) was refluxed for 5 h. The mixture was then evaporated to concentrate to a reddish-black oil. After run flash column using CH2Cl2:MeOH (10:1) as eluent to give a red crystalline solid intermediate, 2,6-dinitro-trans-{circumflex over (α)}-dimethylaminostyrene (20.5 g, yield 86%).

Workup

  1. customThe mixture was then evaporated
  2. concentrationto concentrate to a reddish-black oil

Sources & evidence

ORD record
ord-b2398de1541f4d40b84678882a5f5f15
Source dataset
uspto-grants-2012_04
Patent number
US08147721B2

Reaction notes

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