Anthranilic Acid → 2-(2,4-Dinitroanilino)benzoic acid

HRID 1106413Notes

Reaction equation

HRID 1106413 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[Na+].[Na+].[N+:17]([C:20]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:21]=1F)([O-:19])=[O:18]>O>[N+:17]([C:20]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:21]=1[NH:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 227Anthranilic AcidHCID 6264DinitrofluorobenzeneHCID 10340Sodium Carbonate

Product 1

HCID 6275142-(2,4-Dinitroanilino)benzoic acidYield 92.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

At a bath temperature of 40° C., 1.37 g (10 mmol) of 2-aminobenzoic acid and 2 g (18.7 mmol) of sodium carbonate in 40 ml of water are combined under vigorous stirring with 1.86 g (10 mmol) of 2,4-dinitrofluorobenzene and agitated for 2 hours. The batch is diluted with about 400 ml of water and precipitated with 4N HCl. The product is suctioned off, washed with water, and dried, thus obtaining 2.8 g of 2-(2,4-dinitrophenyl)aminobenzoic acid, mp: 266-270° C.

Workup

  1. customprecipitated with 4N HCl
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-ab3157eedd5449dfb8d5081583764215
Source dataset
uspto-grants-2000_05
Patent number
US06057304

Reaction notes

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