Pyridine → Pyridin-3-yl [2-(2,6-dichloroanilino)phenyl]acetate

HRID 1282918Notes

Reaction equation

HRID 1282918 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:3]=1[NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][C:12]([OH:14])=[O:13].[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[N:20]1[CH:25]=[CH:24][CH:23]=[C:22]([O:13][C:12](=[O:14])[CH2:11][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[NH:4][C:3]2[C:2]([Cl:1])=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:19])[CH:21]=1

Participants

3

Reactant 2

HCID 1049PyridineHCID 3033Diclofenac

Product 1

HCID 21520575Pyridin-3-yl [2-(2,6-dichloroanilino)phenyl]acetate

Procedure

This salt is stirred under nitrogen and anhydrous conditions for 1 hour with 6.5 ml of pyridine and 1.5 g of [o-(2,6-dichloro-anilino)-phenyl]-acetic acid at 20°-30°C and the mixture is then evaporated in vacuo at a maximum temperature of 40°C. The residue is dissolved in 50 ml of ether and while cooling with ice, washed with saturated potassium hydrogen carbonate solution, 1 N-hydrochloric acid, and with ice water. The bulk of the [o-(2,6-dichloro-anilino)-phenyl]-acetic acid-3-pyridyl ester remains in the ether layer and, after this latter has been dried with magnesium sulphate and evaporated in vacuo, is obtained therefrom as a pale brown oil which crystallises on trituration. The new ester contains as impurity 1-(2,6-dichloro-phenyl)-2-hydroxy-indole from which it can be separated by being dissolved in ether/petroleum ether 1:1 and filtered through a silica gel column. The [o-(2,6-dichloro-anilino)-phenyl]-acetic acid-3-pyridyl ester is obtained from the filtered ether/petroleum ether solution (evaporation in vacuo) in the form of colourless crystals which, after precipitation with petroleum ether from an ethereal solution, melt at 84°-86°C.

Workup

  1. customthe mixture is then evaporated in vacuo at a maximum temperature of 40°C
  2. dissolutionThe residue is dissolved in 50 ml of ether
  3. temperaturewhile cooling with ice
  4. washwashed with saturated potassium hydrogen carbonate solution, 1 N-hydrochloric acid
  5. dry with materialafter this latter has been dried with magnesium sulphate
  6. customevaporated in vacuo
  7. customis obtained
  8. customas a pale brown oil which crystallises on trituration
  9. customcan be separated
  10. dissolutionby being dissolved in ether/petroleum ether 1:1
  11. filtrationfiltered through a silica gel column

Sources & evidence

ORD record
ord-c440dfa26ebc4934bf41dae393dd403b
Source dataset
uspto-grants-1976_08
Patent number
US03973024

Reaction notes

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