Anthranilic Acid → Diphenylamine-2,2'-dicarboxylic acid

HRID 280718Notes

Reaction equation

HRID 280718 reaction equation
Cl[C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:11]([OH:20])(=[O:19])[C:12]1[C:13](=[CH:15][CH:16]=[CH:17][CH:18]=1)[NH2:14].C([O-])([O-])=O.[K+].[K+].C(OCCO)C.Cl>O>[C:4]([C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[NH:14][C:13]1[C:12](=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:11]([OH:20])=[O:19])([OH:6])=[O:5]

Participants

7

Reactant 5

HCID 227Anthranilic AcidHCID 313Hydrochloric AcidHCID 8076Glycol monoethyl etherHCID 83742-Chlorobenzoic AcidHCID 11430Potassium Carbonate

Product 1

HCID 11371Diphenylamine-2,2'-dicarboxylic acidYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-chlorobenzoic acid (100 g), anthranilic acid (90 g), anhydrous powered K2CO3 (135 g), Cu/CuO (2 g) and 2-ethoxyethanol (200 ml) was heated with swirling on the steam bath until gas evolution ceased and then stirred at 145° for a further 21/2 hours. The thick reaction mixture was diluted with water, acidified (HCl) and then the crude product was collected and washed well with hot water. This was dissolved in hot dilute aqueous Na2CO3 treated liberally with charcoal-celite and filtered through a celite pad. The hot filtrate was diluted with half the volume of EtOH and then slowly acidified (HCl). The pale yellow product which separated was collected when still warm, washed well with hot water, benzene and dried, providing material (84% yield) of sufficient purity for use in the next step (lit, m.p. 295° dec.).

Workup

  1. temperaturewas heated
  2. customthe crude product was collected
  3. washwashed well with hot water
  4. dissolutionThis was dissolved in hot dilute aqueous Na2CO3
  5. additiontreated liberally with charcoal-celite
  6. filtrationfiltered through a celite pad
  7. additionThe hot filtrate was diluted with half the volume of EtOH
  8. customThe pale yellow product which separated
  9. customwas collected when
  10. temperaturestill warm
  11. washwashed well with hot water, benzene
  12. customdried

Sources & evidence

ORD record
ord-67717673b7ea41708eaac0b354a893dc
Source dataset
uspto-grants-1986_05
Patent number
US04590277

Reaction notes

Loading…