2-Chloroaniline → HCID 13138307, compound

HRID 354791Notes

Reaction equation

HRID 354791 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].Br[C:10]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=[O:13].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][C:10]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=[O:13]

Participants

5

Reactant 3

HCID 72402-ChloroanilineHCID 11430Potassium CarbonateHCID 684522-Bromo-3-nitrobenzoic acid

Product 1

HCID 13138307HCID 13138307, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of the known compounds 2-chloroaniline (6.3 g., 0.05 mole) and 2-bromo-3-nitrobenzoic acid (12.3 g., 0.05 mole) was refluxed overnight with 11 g. of potassium carbonate and 0.5 g. of copper-bronze in 125 ml. of ethanol. The ethanol was then removed by evaporation and the residue suspended in water. After filtration, the filtrate was acidified. A solid slowly crystallized, providing the compound 2-(2-chloroanilino)-3-nitrobenzoic acid, m.p. 213°-215° C.

Workup

  1. temperaturewas refluxed overnight with 11 g
  2. customThe ethanol was then removed by evaporation
  3. filtrationAfter filtration
  4. customA solid slowly crystallized

Sources & evidence

ORD record
ord-a591580c2acb42c0a8564953dab7c164
Source dataset
uspto-grants-1983_03
Patent number
US04377579

Reaction notes

Loading…