Potassium Carbonate → 2-[4-(Benzyloxy)anilino]-5-methoxybenzoic acid

HRID 2413268Notes

Reaction equation

HRID 2413268 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl.[CH2:14]([O:21][C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)CCCC.[Cu]>[CH2:14]([O:21][C:22]1[CH:23]=[CH:24][C:25]([NH:26][C:2]2[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])=[CH:27][CH:28]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 899062-Bromo-5-methoxybenzoic acidHCID 27238314-Benzyloxyaniline hydrochloride

Product 1

HCID 133714622-[4-(Benzyloxy)anilino]-5-methoxybenzoic acidYield 70.1%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 62761-PentanolSolvent

Procedure

A mixture of 231 g of 2-bromo-5-methoxybenzoic acid, 262 g of 4-benzyloxyaniline hydrochloride, 160 g of potassium carbonate and 2 g of activated copper powder in about 2100 ml of amyl alcohol was heated at reflux with stirring for 4.5 hours. The reaction mixture was concentrated in vacuo and the residue dissolved in 6 liters of water. The solution was filtered and acidified with hydrochloric acid. The solid which formed was collected and recrystallized twice from benzene-cyclohexane to give 245 g of 2-(4-benzyloxyphenylamino)-5-methoxybenzoic acid, m.p. 167°-168° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. dissolutionthe residue dissolved in 6 liters of water
  5. filtrationThe solution was filtered
  6. customThe solid which formed
  7. customwas collected
  8. customrecrystallized twice from benzene-cyclohexane

Sources & evidence

ORD record
ord-9bad9a42fff84583b93ca3bc764951f4
Source dataset
uspto-grants-1985_01
Patent number
US04496590

Reaction notes

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