Hydrochloric Acid → Amino-5,6-dichloro-3-nitrobenzoic acid

HRID 487195

Reaction equation

HRID 487195 reaction equation
[N+:1]([C:4]1[C:5](Cl)=[C:6]([C:10]([Cl:14])=[C:11]([Cl:13])[CH:12]=1)[C:7]([OH:9])=[O:8])([O-:3])=[O:2].ClC1C=CC=CC=1C[NH2:20].Cl>C1(C)C=CC=CC=1>[NH2:20][C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:12][C:11]([Cl:13])=[C:10]([Cl:14])[C:6]=1[C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 666482-ChlorobenzylamineHCID 190942393-Nitro-2,5,6-trichlorobenzoic acid

Product 1

HCID 131718350Amino-5,6-dichloro-3-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 3-nitro-2,5,6-trichlorobenzoic acid (37.1 mmol, 10.0 g) in 150 mL of toluene, was added 2-chlorobenzylamine (81.6 mmol, 11.56 g). The reaction mixture was refluxed overnight, poured into dilute hydrochloric acid and vigorously stirred. The resulting solid was filtered. The product was dissolved in toluene and then precipitated with diethyl ether. Recrystallization of the product from methanol gave 3.4 g of 2-[2-chlorophenyl)methyl]amino-5,6-dichloro-3-nitrobenzoic acid; mp 168.5°-171° C.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. filtrationThe resulting solid was filtered
  3. dissolutionThe product was dissolved in toluene
  4. customprecipitated with diethyl ether
  5. customRecrystallization of the product from methanol

Sources & evidence

ORD record
ord-2acbb49479fc4ff59a140401e97e8c33
Source dataset
uspto-grants-1994_03
Patent number
US05294631

Linked notes

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