P-Phenylenediamine → 2-(4-Aminoanilino)-5-nitrobenzoic acid

HRID 1593934Notes

Reaction equation

HRID 1593934 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:14]1([NH2:21])[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>[Cu].O>[NH2:20][C:17]1[CH:18]=[CH:19][C:14]([NH:21][C:2]2[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 7814P-PhenylenediamineHCID 11430Potassium CarbonateHCID 172872-Chloro-5-nitrobenzoic acid

Product 1

HCID 210740702-(4-Aminoanilino)-5-nitrobenzoic acidYield 64.2%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent

Procedure

A mixture of 2-chloro-5-nitrobenzoic acid 9 (150 g, 0.744 mol), 1,4-phenylenediamine 8 (150.0 g, 1.387 mol), anhydrous potassium carbonate (309 g, 2.236 mol), copper powder (2.0 g, 31.5 mol), cupric sulfate (10 mg) and water (2.25 l) was heated to reflux with stirring for 5 hr. It was then filtered hot through a fluted paper and allowed to stand overnight at room temperature. The potassium salt of the product was collected on a glass sinter and washed with ice-cold water (2×250 mL) followed by ice-cold ethanol (250 mL). The product was dissolved in boiling water (1250 mL) and acetic acid was then added until there was no further precipitation. The mixture was cooled with an external ice water bath and the product collected. The product was washed with ice-cold water (3×500 mL) followed by ice-cold ethanol (2×500 mL), dry ether (250 mL) and finally hexane (2×500 mL). The product was dried over P2O5 under vacuum to yield a light brown solid 10 (130.52 g 64%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. filtrationIt was then filtered hot through a fluted paper
  4. waitto stand overnight at room temperature
  5. customThe potassium salt of the product was collected on a glass sinter
  6. washwashed with ice-cold water (2×250 mL)
  7. dissolutionThe product was dissolved
  8. additionwas then added until there
  9. customno further precipitation
  10. temperatureThe mixture was cooled with an external ice water bath
  11. customthe product collected
  12. washThe product was washed with ice-cold water (3×500 mL)
  13. dry with materialThe product was dried over P2O5 under vacuum

Sources & evidence

ORD record
ord-fc63118db3f240d3a9999f1e1c559c69
Source dataset
uspto-grants-2007_11
Patent number
US07300930B2

Reaction notes

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