Kojic Acid → HCID 12468238, compound

HRID 1514663Notes

Reaction equation

HRID 1514663 reaction equation
[CH:1]1[C:6](=[O:7])[C:5]([OH:8])=[CH:4]O[C:2]=1[CH2:9][OH:10].[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>Cl>[OH:8][C:5]1[C:6](=[O:7])[CH:1]=[C:2]([CH2:9][OH:10])[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 3840Kojic AcidHCID 6115Aniline

Product 1

HCID 12468238HCID 12468238, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of kojic acid (1.421 g, 10.00 mmol) in diluted hydrochloric acid (0.52 mL of concentrated hydrochloric acid diluted with 25 mL of water) was added aniline (1.40 mL, 15.4 mmol). The resulting mixture was heated under reflux for 20 h. The mixture, while warm (60° C.), was washed with dichloromethane two times and the organic phase was discarded. The aqueous phase was neutralized with solid sodium carbonate, upon which much off-white precipitate appeared. The mixture stood in a hood overnight. The crude product was isolated by filtration and purified by recrystallization with methanol to give a pale solid (1.064 g, 49%). Mp: 236-238° C. (lit.85 237-240° C.). 1H NMR (d6-DMSO): δ 4.20 (2H, s), 6.47 (1H, s), 7.35 (1H, s), 7.5-7.6 (5H, m). 13C NMR (d6-DMSO): δ 70.9, 102.5, 114.8, 118.2, 118.9, 130.5, 138.7, 146.7, 165.3, 179.5.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 20 h
  3. washwas washed with dichloromethane two times
  4. customThe crude product was isolated by filtration
  5. custompurified by recrystallization with methanol

Sources & evidence

ORD record
ord-ac3942ae0c9141909b8cab2845e39904
Source dataset
uspto-grants-2012_07
Patent number
US08222279B2

Reaction notes

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