HCID 70479432, compound → HCID 57131503, compound

HRID 464710Notes

Reaction equation

HRID 464710 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][CH:10]([O:21][C:22](=[O:30])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:11]([O:13]CC1C=CC=CC=1)=[O:12]>C(O)(=O)C.[Pd]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][CH:10]([O:21][C:22](=[O:30])[CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:11]([OH:13])=[O:12]

Participants

4

Reactant 1

HCID 70479432HCID 70479432, compound

Product 1

HCID 57131503HCID 57131503, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
40 °C

Procedure

32 g (0.072 moles) of benzyl 2-[(2,6-dichlorophenyl)amino]phenylacetoxyacetate prepared above were dissolved in 1000 ml of acetic acid, and the resulting mixture was mixed with 5 g of Pd/C 10% and then hydrogenated at a pressure of 3 atmospheres under heating to a temperature of 40° C. for a period of 10 hours. The catalyst was filtered, and the resulting solution was concentrated and then washed with toluene to remove acetic acid. The product was then recrystallized from cyclohexane, thus obtaining 13 g (50%) of 2-[(2,6-dichlorophenyl)amino]phenylacetoxyacetic acid, in the form of white crystals having a melting point of 149°-150° C., Rf=0.51 (acetone 100/acetic acid 2.5). Spectral data and elemental analysis of the product were as follows.

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe resulting solution was concentrated
  3. washwashed with toluene
  4. customto remove acetic acid
  5. customThe product was then recrystallized from cyclohexane

Sources & evidence

ORD record
ord-05a17e2af00e43fb8d7f7ab2306410da
Source dataset
uspto-grants-1985_10
Patent number
US04548952

Reaction notes

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