Methane → Anthranilic acid, N-(p-fluorophenyl)-

HRID 1662932Notes

Reaction equation

HRID 1662932 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.Cl[C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=[O:13].C(=O)([O-])[O-].[Na+].[Na+].C>O.C(O)CO>[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:10]2[C:11](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:12]([OH:14])=[O:13])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 297MethaneHCID 83742-Chlorobenzoic AcidHCID 97314-FluoroanilineHCID 10340Sodium Carbonate

Product 1

HCID 120159Anthranilic acid, N-(p-fluorophenyl)-Yield 37.3%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 962WaterSolvent2×

Conditions

Temperature
125 °C

Procedure

4-Fluoroaniline (1.86 gm; 20 mmol), 2-chlorobenzoic acid (1.56 gm; 10 mmol), ethylene glycol (5 ml) and anhydrous sodium carbonate (1.1 gm; 10 mmol) were placed in a reaction vessel and stirred until effervescence ceased. Cupric chloride (100 mg; 0.75 mmol) dissolved in 2 ml of water was added to the reaction mixture which was then heated to 125° C. for 6 hrs. The reaction was allowed to cool and water (30 ml) and charcoal were added. The mixture was filtered and then acidified to pH 2 with conc. hydrochloric acid. The precipitate was collected by filtration, washed with water and then re-dissolved in 1M sodium hydroxide solution. Material was re-precipitated by the addition of acetic acid, filtered off, washed with aqueous acetic acid, then water and finally dried under vacuum over phosphorous pentoxide to give 862 mg (37%) of N-(4-fluorophenyl)anthranilic acid.

Workup

  1. additionwas added to the reaction mixture which
  2. temperatureto cool
  3. filtrationThe mixture was filtered
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water
  6. dissolutionre-dissolved in 1M sodium hydroxide solution
  7. customMaterial was re-precipitated by the addition of acetic acid
  8. filtrationfiltered off
  9. washwashed with aqueous acetic acid
  10. dry with materialwater and finally dried under vacuum over phosphorous pentoxide

Sources & evidence

ORD record
ord-2389d2a8cc544a1986a43562ae7c2298
Source dataset
uspto-grants-2011_10
Patent number
US08034558B2

Reaction notes

Loading…