Glycolic Acid → HCID 178423977, compound

HRID 1953733Notes

Reaction equation

HRID 1953733 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([CH3:9])[CH:5]=[C:4]([CH3:10])[N:3]=1.[C:11](O)(=O)[CH2:12][OH:13]>C1(C)C=CC=CC=1>[OH:13][CH2:12][C:11]1[NH:1][C:2]2[C:7]([N:8]=1)=[C:6]([CH3:9])[CH:5]=[C:4]([CH3:10])[N:3]=2

Participants

4

Reactant 2

HCID 757Glycolic AcidHCID 110299024,6-Dimethylpyridine-2,3-diamine

Product 1

HCID 178423977HCID 178423977, compoundYield 15.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of 13.72 g of 2,3-diamino-4,6-dimethylpyridine and 25 g of glycolic acid in 200 ml of toluene was heated under reflux for 3.5 hours, whilst distilling off azeotropically the water formed in the course of the reaction. At the end of this time, the reaction mixture was freed from the toluene by decantation and the oily residue was purified by column chromatography through silica gel, using a gradient elution method, with mixtures of ethanol and ethyl acetate in ratios ranging from 2:3 to 1:1 by volume as a eluent, to give 2.7 g of the title compound, melting at 244-246° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3.5 hours
  3. distillationwhilst distilling off azeotropically the water
  4. customformed in the course of the reaction
  5. customthe oily residue was purified by column chromatography through silica gel
  6. washa gradient elution method

Sources & evidence

ORD record
ord-a80b2b4bd17946639e0a5599033d06f9
Source dataset
uspto-grants-2000_09
Patent number
US06117893

Reaction notes

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