Glycolic Acid → HCID 178526485, compound

HRID 1916612Notes

Reaction equation

HRID 1916612 reaction equation
[C:1]([OH:5])(=O)[CH2:2]O.[N+:6]([C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([NH2:16])[CH:10]=1)([O-:8])=[O:7].[OH-].[Na+]>Cl.O>[N+:6]([C:9]1[CH:14]=[CH:13][C:12]2[NH:15][C:2]([CH2:1][OH:5])=[N:16][C:11]=2[CH:10]=1)([O-:8])=[O:7]

Participants

6

Reactant 3

HCID 757Glycolic AcidHCID 14798Sodium HydroxideHCID 51117914-Nitro-1,2-phenylenediamine

Product 1

HCID 178526485HCID 178526485, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

6.2 g (81.5 mmol) glycolic acid is added to a solution of 6.24 g (40.8 mmol) 4-nitro-o-phenylenediamine in 80 mL semiconcentrated HCl. The reaction solution is refluxed for 4 h and the solvent is eliminated i.vac. The residue is taken up in water and made basic with 2 N NaOH. The product precipitates out and is stirred for another 1 hour in the ice bath. The precipitate is suction filtered and washed successively with water and PE. The product is dried at 40° C. This still contains 40% 4-nitro-o-phenylenediamine. It is again taken up in semiconcentrated HCl and after the addition of 6.5 mL glycolic acid (57% in water) it is refluxed for 3 h and heated for a further 12 h at 80° C. The solvent is eliminated i.vac. and the residue is dissolved in water and made alkaline with 6 N NaOH, during which time the product is precipitated. The precipitate is suction filtered and washed successively with water and PE. The product is dried in the circulating air dryer at 50° C.

Workup

  1. temperatureThe reaction solution is refluxed for 4 h
  2. customThe product precipitates out
  3. filtrationfiltered
  4. washwashed successively with water and PE
  5. customThe product is dried at 40° C
  6. additionafter the addition of 6.5 mL glycolic acid (57% in water) it
  7. temperatureis refluxed for 3 h
  8. dissolutionand the residue is dissolved in water
  9. customduring which time the product is precipitated
  10. filtrationfiltered
  11. washwashed successively with water and PE
  12. customThe product is dried in the circulating air dryer at 50° C.

Sources & evidence

ORD record
ord-d4ba8a1c0af94be69da4adea95160aad
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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