Dinitrofluorobenzene → HCID 44254850, compound

HRID 2089272Notes

Reaction equation

HRID 2089272 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].F[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:17]=1[N+:25]([O-:27])=[O:26]>CN(C=O)C.O>[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][C:20]2[CH:21]=[CH:16][C:17]([N+:25]([O-:27])=[O:26])=[CH:18][C:19]=2[N+:22]([O-:24])=[O:23])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6264DinitrofluorobenzeneHCID 4278144-AminobenzylamineHCID 516892Sodium Bicarbonate

Product 1

HCID 44254850HCID 44254850, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-aminobenzylamine (25.5 mL, 225 mmol) and powdered NaHCO3 (94.5 g, 1125 mmol) in anhydrous DMF (300 mL) was added 2,4-dinitrofluorbenzene (1) (18.8 mL, 150 mmol) dropwise at room temperature. After 2 hours, the solution was slowly diluted with water (1000 mL) to precipitate the product, which was collected on a fritted funnel while rinsing with water until the eluent was colorless. The solid was further dried under high vacuum to afford 43.0 g as a bright orange solid in 99% yield.

Workup

  1. customto precipitate the product, which
  2. customwas collected on a fritted funnel
  3. washwhile rinsing with water until the eluent
  4. customThe solid was further dried under high vacuum
  5. customto afford 43.0 g as a bright orange solid in 99% yield

Sources & evidence

ORD record
ord-b8e83baaac9c41fc924a8bc79a0754ed
Source dataset
uspto-grants-2013_05
Patent number
US08436031B2

Reaction notes

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