Toluene → Diclofenac

HRID 1449239Notes

Reaction equation

HRID 1449239 reaction equation
C1(C)C=CC=CC=1.C([N:15]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH2:30][C:31]([OH:33])=[O:32])[C:16]1[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:17]=1[Cl:23])C1C=CC=CC=1>ClC1C=CC=CC=1Cl>[Cl:22][C:21]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:23])[C:16]=1[NH:15][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH2:30][C:31]([OH:33])=[O:32]

Participants

4

Reactant 2

HCID 1140TolueneHCID 13023173HCID 13023173, compound

Product 1

HCID 3033DiclofenacYield 91.3%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

In an autoclave, 55 ml of toluene, 4 ml of o-dichlorobenzene, 10.0 g of N-benzyl-o-(2,6-dichloroanilino)phenylacetic acid and 2.0 g of 5% Pd-alumina were charged and it was purged with hydrogen gas and hydrogen gas was fed at 70° to 75° C. under a pressure of 10 to 20 cm H2O for 1.5 hours. The reaction mixture at the same temperature was filtered to remove 5% Pd-alumina and catalyst was washed with 35 ml of THF. The filtrate and the washing were combined and THF and toluene were distilled off. The residue was admixed with 200 ml of n-hexane and cooled to obtain 7.0 g of o-(2,6-dichloroanilino)phenylacetic acid as colorless crystals. Yield: 91.2%

Workup

  1. customit was purged with hydrogen gas and hydrogen gas
  2. filtrationThe reaction mixture at the same temperature was filtered
  3. customto remove 5% Pd-alumina and catalyst
  4. washwas washed with 35 ml of THF
  5. distillationTHF and toluene were distilled off
  6. temperaturecooled

Sources & evidence

ORD record
ord-40f671c11d0745ceb2e0acd7e197a53c
Source dataset
uspto-grants-1980_02
Patent number
US04189595

Reaction notes

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