Water → N-(3-Carboxyphenyl)-4-(3-furanyl)-2-nitroaniline

HRID 581951Notes

Reaction equation

HRID 581951 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:15]=[CH:14][O:13][CH:12]=2)=[CH:7][C:6]=1[N+:16]([O-:18])=[O:17])(=O)[CH3:2].I[C:20]1[CH:21]=[C:22](C=C[CH:28]=1)[C:23]([OH:25])=[O:24].C(=O)([O-])[O-].[K+].[K+].O>CN1CCCC1=O>[C:23]([C:22]1[CH:2]=[C:1]([NH:4][C:5]2[CH:10]=[CH:9][C:8]([C:11]3[CH:15]=[CH:14][O:13][CH:12]=3)=[CH:7][C:6]=2[N+:16]([O-:18])=[O:17])[CH:28]=[CH:20][CH:21]=1)([OH:25])=[O:24]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 120603-Iodobenzoic acidHCID 54094756N-Acetyl 4-(3-furanyl)-2-nitroaniline

Product 1

HCID 54219463N-(3-Carboxyphenyl)-4-(3-furanyl)-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 1e from Example 19 (5 g, 24.5 mmol), 3-iodobenzoic acid (6.69 g, 27 mmol), potassium carbonate (3.79 g, 27.5 mmol) and a catalytic amount of copper-bronze in 30 ml dry N-methyl-2-pyrrolidone is heated to 180° C. overnight. After cooling water is added and the mixture is washed twice with ethyl acetate. The aqueous phase is rendered acidic with diluted hydrochloric acid and the oily precipitate is filtered off. This precipitate is extracted with ethyl acetate, and the extract is purified by column-chromatography on silica gel using a mixture of ethyl acetate and petroleum ether (1:1) as the eluent. Yield: 2.56 g (32%). Mp 203-205° C.

Workup

  1. additionis added
  2. washthe mixture is washed twice with ethyl acetate
  3. filtrationthe oily precipitate is filtered off
  4. extractionThis precipitate is extracted with ethyl acetate
  5. customthe extract is purified by column-chromatography on silica gel using
  6. additiona mixture of ethyl acetate and petroleum ether (1:1) as the eluent

Sources & evidence

ORD record
ord-64b18ac42eef4ed4a22862b1edab773d
Source dataset
uspto-grants-1999_07
Patent number
US05922724

Reaction notes

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