Water → HCID 18315423, compound

HRID 1699858Notes

Reaction equation

HRID 1699858 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([OH:7])=[O:6].[Cl:14][C:15]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:16]=1[CH2:17][NH2:18].C1(C)C=CC=CC=1.O>C(OCC)(=O)C>[Cl:14][C:15]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:16]=1[CH2:17][NH:18][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([OH:7])=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 14852,4-DichlorobenzylamineHCID 2306533-Fluoro-4-nitrobenzoic acid

Product 1

HCID 18315423HCID 18315423, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-fluoro-4-nitrobenzoic acid (5.20 g), 2,4-dichlorobenzyl-amine (14.8 g) and toluene (35 ml) was refluxed under heating for 24 hr. The mixture was heated to room temperature, and water and ethyl acetate were added. The mixture was stirred and precipitated crystals were collected by filtration. The chloroform layer of the filtrate was separated and the solvent was distilled away. Ether was added to the residue and the precipitated crystals were collected by filtration. The crystals were combined, washed with ether and dried to give 3-(2,4-dichlorobenzyl-amino)-4-nitrobenzoic acid. Sulfuric acid (2.3 g) was added thereto, and the mixture was refluxed under heating in ethanol for 6 hr. The reaction mixture was concentrated and poured into a saturated aqueous solution of sodium hydrogencarbonate. The mixture was extracted with ethyl acetate, washed with saturated brine and dried. The solvent was distilled away and the residue was crystallized from a mixed solvent of ethyl acetate and hexane. The crystals were collected by filtration and dried to give the objective compound (4.0 g).

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 24 hr
  3. customprecipitated crystals
  4. filtrationwere collected by filtration
  5. customThe chloroform layer of the filtrate was separated
  6. distillationthe solvent was distilled away
  7. additionEther was added to the residue
  8. filtrationthe precipitated crystals were collected by filtration
  9. washwashed with ether
  10. customdried

Sources & evidence

ORD record
ord-2ea2861cab8d4a46996a24dfbd94ba46
Source dataset
uspto-grants-2002_02
Patent number
US06348474B1

Reaction notes

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