1-Pentanol → 2-[(4-Methoxyphenyl)amino]benzoic acid

HRID 1731014Notes

Reaction equation

HRID 1731014 reaction equation
Cl[C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].C(O)CCCC>[Cu]>[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:2]2[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]([OH:6])=[O:5])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 62761-PentanolHCID 7732P-AnisidineHCID 83742-Chlorobenzoic AcidHCID 11430Potassium Carbonate

Product 1

HCID 2029182-[(4-Methoxyphenyl)amino]benzoic acid

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

A mixture of 80 g. 2-chlorobenzoic acid, 80 g. 4-anisidine, 80 g. potassium carbonate, 4 g. activated copper powder, and 800 ml. amyl alcohol was heated under reflux with efficient stirring for four hours. The amyl alcohol was removed by steam distillation and the remaining aqueous phase was filtered and made neutral by addition of 1:1 concentrated hydrochloric acid-water. The resulting solid (102 g.) was collected by filtration to give after recrystallization from isopropyl alcohol N-(4-methoxyphenyl)anthranilic acid; m.p. 183°-184°C.

Workup

  1. additionA mixture of 80 g
  2. temperatureunder reflux
  3. customThe amyl alcohol was removed by steam distillation
  4. filtrationthe remaining aqueous phase was filtered
  5. additionmade neutral by addition of 1:1 concentrated hydrochloric acid-water
  6. filtrationThe resulting solid (102 g.) was collected by filtration
  7. customto give
  8. customafter recrystallization from isopropyl alcohol N-(4-methoxyphenyl)anthranilic acid

Sources & evidence

ORD record
ord-0308aad511a24d9bad5575c8f92c03a2
Source dataset
uspto-grants-1976_11
Patent number
US03994902

Reaction notes

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