Water → 2,4-Dinitro-N,N-dipropylaniline

HRID 896731Notes

Reaction equation

HRID 896731 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1F)([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+].[CH2:20]([NH:23][CH2:24][CH2:25][CH3:26])[CH2:21][CH3:22].O>CN1C(=O)CCC1>[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[N:23]([CH2:24][CH2:25][CH3:26])[CH2:20][CH2:21][CH3:22])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6264DinitrofluorobenzeneHCID 8902DipropylamineHCID 11430Potassium Carbonate

Product 1

HCID 157580702,4-Dinitro-N,N-dipropylanilineYield 98%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

To an ice cooled solution of 2,4-dinitrofluorobenzene (9.3 g, 50 mmol) and K2CO3 (6.9 g, 50 mmol) in 40 ml NMP was added dropwise dipropylamine (6.07 g, 60 mmol) in 10 ml NMP. After stirring for 1 hr, the reaction mixture was poured into a separatory funnel containing 100 ml water and extracted 3×100 mls with ether. The combined organics were washed with 3×100 ml water, 100 ml brine, dried with anhydrous MgSO4 and concentrated, giving 13.1 g crude product. This material was pure enough to carry on to the next step.

Workup

  1. additionthe reaction mixture was poured into a separatory funnel
  2. extractionextracted 3×100 mls with ether
  3. washThe combined organics were washed with 3×100 ml water, 100 ml brine
  4. dry with materialdried with anhydrous MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-af35f6ac0f994cc1a26600bcbf62900d
Source dataset
uspto-grants-2005_07
Patent number
US06919404B2

Reaction notes

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