Citric Acid → HCID 14579763, compound

HRID 1534201Notes

Reaction equation

HRID 1534201 reaction equation
[OH:1][C:2]1[C:7]2[C:8]([CH3:19])=[C:9]([C:11](=O)[C:12]3[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=3)[O:10][C:6]=2[CH:5]=[CH:4][C:3]=1[CH2:20][CH2:21][CH3:22].[OH-].[K+].NN.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)CO>[OH:1][C:2]1[C:7]2[C:8]([CH3:19])=[C:9]([CH2:11][C:12]3[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=3)[O:10][C:6]=2[CH:5]=[CH:4][C:3]=1[CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 9321HydrazineHCID 14797Potassium HydroxideHCID 14579762HCID 14579762, compound

Product 1

HCID 14579763HCID 14579763, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
155 °C

Procedure

A mixture of 4-hydroxy-3-methyl-5-propyl-2-(isonicotinoyl)-benzofuran (1.5 g; 5.2 mmoles), potassium hydroxide pellets (2 g; 37 mmoles), ethylene glycol (25 ml) and 99% hydrazine (0.8 ml) was heated with stirring at 130° C. for 1 hour and at 155° C. for 2 hours. The mixture was cooled and acidified with 20% citric acid solution. The mixture was extracted using 20% ethyl acetate in diethyl ether. The organic layer was dried (Na2SO4), filtered, concentrated, and chromatographed to obtain 1 g of the title compound which was then recrystallized from ethyl acetate.

Workup

  1. temperaturewas heated
  2. temperatureThe mixture was cooled
  3. extractionThe mixture was extracted
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customchromatographed

Sources & evidence

ORD record
ord-c0d5d01b62294e68874804c73bd74485
Source dataset
uspto-grants-1992_02
Patent number
US05087638

Reaction notes

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