Glycolic Acid → HCID 178519930, compound

HRID 1030519Notes

Reaction equation

HRID 1030519 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:9].[C:10](O)(=O)[CH2:11][OH:12].[OH-].[Na+]>>[OH:9][C:3]1[C:2]2[NH:1][C:10]([CH2:11][OH:12])=[N:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 757Glycolic AcidHCID 14798Sodium HydroxideHCID 5799372,3-Diaminophenol

Product 1

HCID 178519930HCID 178519930, compoundYield 54.6%

Procedure

To a solution of 40 ml 4M CHl 1.1 g (0.0087 mol) of 2,3-diaminophenol and 2 g (0.026 mol) of glycolic acid were added and the solution was heated under reflux for 20 h. Upon cooling the reaction mixture was alkalized with 10M NaOH to pH 8.5. The volatiles were removed under reduced pressure and the residual oil was suspended in methanol. The suspension was filtered and evaporated to dryness in vacuo. Chromatography on silica gel and elution with methylene chloride:methanol (10:2) gave 0.78 g of the title compound.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 20 h
  3. temperatureUpon cooling the reaction mixture
  4. customThe volatiles were removed under reduced pressure
  5. filtrationThe suspension was filtered
  6. customevaporated to dryness in vacuo
  7. washChromatography on silica gel and elution with methylene chloride:methanol (10:2)

Sources & evidence

ORD record
ord-1f0d8ce64a9f490d84cc8a2e13b021bb
Source dataset
uspto-grants-1992_04
Patent number
US05106862

Reaction notes

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