Diethyl Ether → 5-bromo-2-[(2-chlorophenyl)methyl]amino-3-nitrobenzoic Acid

HRID 273836Notes

Reaction equation

HRID 273836 reaction equation
Br[C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([Br:14])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Cl:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH2:18][NH2:19].[OH-].[Na+].CCOCC>C1(C)C=CC=CC=1>[Br:14][C:8]1[CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:2]([NH:19][CH2:18][C:17]2[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=2[Cl:15])=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 666482-ChlorobenzylamineHCID 193515522,5-dibromo-3-nitrobenzoic Acid

Product 1

HCID 193585455-bromo-2-[(2-chlorophenyl)methyl]amino-3-nitrobenzoic AcidYield 61.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 2,5-dibromo-3-nitrobenzoic acid (10.76 g, 0.0331 mol) in toluene (100 mL) was placed under argon, treated with 2-chlorobenzylamine (14.06 g, 0.0993 mol) and the mixture was brought to reflux. A clear, red solution resulted and the solution was refluxed for 24 hours, cooled, poured into 5% sodium hydroxide solution (600 mL) and ether (100 mL). The insoluble material was filtered off, the layers separated and the aqueous phase was added to the insoluble material and acidified with 10% hydrochloric acid solution. The separated crystalline product was collected, washed with water and the solid was crystallized from a large volume of methanol to provide 7.85 g (61.5%) of the yellow crystalline 5-bromo-2-[(2-chlorophenyl)methyl]amino-3-nitrobenzoic acid; mp 159°-161° C.

Workup

  1. temperatureto reflux
  2. customA clear, red solution resulted
  3. temperaturethe solution was refluxed for 24 hours
  4. temperaturecooled
  5. filtrationThe insoluble material was filtered off
  6. customthe layers separated
  7. additionthe aqueous phase was added to the insoluble material
  8. customThe separated crystalline product was collected
  9. washwashed with water
  10. customthe solid was crystallized from a large volume of methanol

Sources & evidence

ORD record
ord-630a5772fbe442e79cef8b0a39a8d6c6
Source dataset
uspto-grants-1995_02
Patent number
US05387601

Reaction notes

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