Acetic Acid → HCID 54370809, compound

HRID 261509Notes

Reaction equation

HRID 261509 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:3]=1[NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11](=[O:16])[C:12]([O:14][CH3:15])=[O:13].C(O)(=O)C.C(O)(=O)C.CO>CO>[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:3]=1[NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH:11]([OH:16])[C:12]([O:14][CH3:15])=[O:13]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10129899Acetic acid methanolHCID 54013338HCID 54013338, compound

Product 1

HCID 54370809HCID 54370809, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3.24 g of methyl 2-(2,6-dichloroanilino)-phenylglyoxylate in 50 ml of a 0.1 N acetic acid solution in methanol (hereinafter often referred to as "0.1 N acetic acid/methanol") was added 0.6 g of 5% Pt-carbon, and vigorous stirring was effected at room temperature under a hydrogen pressure of 2 atmospheres for 10 hours. The catalyst was filtered off and the filtrate was concentrated at room temperature under a reduced pressure of 10 mmHg. The crystalline substance thus deposited was recovered by filtration and recrystallized from ethanol to give 3.0 g of methyl 2-(2,6-dichloroanilino)phenylglycolate. m.p. 123°-124.5° C.

Workup

  1. customwas effected at room temperature under a hydrogen
  2. customfor 10 hours
  3. filtrationThe catalyst was filtered off
  4. concentrationthe filtrate was concentrated at room temperature under a reduced pressure of 10 mmHg
  5. filtrationThe crystalline substance thus deposited was recovered by filtration
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-bdefa1c56f114d3e85dc20fa2d39f4f0
Source dataset
uspto-grants-1979_08
Patent number
US04166128

Reaction notes

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