Aniline → N-Phenylanthranilic Acid

HRID 1730829Notes

Reaction equation

HRID 1730829 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=[O:12].C(=O)([O-])[O-].[K+].[K+]>>[C:2]1([NH:1][C:9]2[C:10](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:11]([OH:13])=[O:12])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6115AnilineHCID 83742-Chlorobenzoic AcidHCID 11430Potassium Carbonate

Product 1

HCID 4386N-Phenylanthranilic Acid

Procedure

Redistilled aniline (310 g, 3.32 mol), pure 2-chlorobenzoic acid (82 g, 0.52 mol), fresh dried potassium carbonate (82 g, 0.6 mol) and cupric oxide (2.0 g) are refluxed for two hours in an oil bath (air cooler). Excess aniline is initially removed by distillation in vacuum and later by water vapor. The remaining solution (500 ml) is boiled for 15 min. with 40 g of activated carbon and filtrated. The filtrate is poured into a mixture of concentrated hydrochloric acid (60 ml) and water (120 ml) during agitation. After cooling the deposit is separated by filtration, washed in water and dried at 120° C. This blue-grey product is cleaned out by dissolving 50 g in 1000 ml of water containing 25 g of sodium carbonate and boiling for 5 minutes with 25 g activated carbon. This is followed by filtration and precipitation with concentrated hydrochloric acid (vigorous foaming). The deposit is separated by filtration, washed in water and dried at 120° C.

Workup

  1. temperatureare refluxed for two hours in an oil bath (air cooler)
  2. customExcess aniline is initially removed by distillation in vacuum and later by water vapor
  3. filtrationfiltrated
  4. additionThe filtrate is poured into a mixture of concentrated hydrochloric acid (60 ml) and water (120 ml) during agitation
  5. temperatureAfter cooling the deposit
  6. customis separated by filtration
  7. washwashed in water
  8. customdried at 120° C
  9. dissolutionby dissolving 50 g in 1000 ml of water containing 25 g of sodium carbonate
  10. waitboiling for 5 minutes with 25 g
  11. filtrationThis is followed by filtration and precipitation with concentrated hydrochloric acid (vigorous foaming)
  12. customThe deposit is separated by filtration
  13. washwashed in water
  14. customdried at 120° C.

Sources & evidence

ORD record
ord-aa41663de68b450da3866cceb85d5ab3
Source dataset
uspto-grants-1976_11
Patent number
US03994688

Reaction notes

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