Ethanol → HCID 15408136, compound

HRID 2182499Notes

Reaction equation

HRID 2182499 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]2[O:18][C:19]([C:22]([OH:24])=[O:23])=[CH:20][CH:21]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[K].[CH2:26](O)[CH3:27].S(=O)(=O)(O)O>C1(C)C=CC=CC=1.O>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]2[O:18][C:19]([C:22]([O:24][CH2:26][CH3:27])=[O:23])=[CH:20][CH:21]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 5462222PotassiumHCID 10925187HCID 10925187, compound

Product 1

HCID 15408136HCID 15408136, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

52.4 g (0.15 mol) of 1-benzyl-3-(5-carboxy-2-furyl)indazole, potassium salt, were initially charged in 1250 ml of toluene, and after addition of 200 ml of abs. ethanol and 50 ml of conc. sulfuric acid the mixture was stirred under reflux on a water separator. After 3 hours, the mixture was concentrated using a rotary evaporator, the oil that remained was taken up in water/ethyl acetate and the aqueous phase was separated off. The organic phase was washed with water and 7.5% strength NaHCO3 solution, dried with sodium sulfate and concentrated. The residue was recrystallized from isopropanol. This gave 37.8 g (73%) of the title compound. m.p.: 98-99° C.

Workup

  1. additionafter addition of 200 ml of abs
  2. concentrationthe mixture was concentrated
  3. customa rotary evaporator
  4. customthe aqueous phase was separated off
  5. washThe organic phase was washed with water and 7.5% strength NaHCO3 solution
  6. dry with materialdried with sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was recrystallized from isopropanol

Sources & evidence

ORD record
ord-951461b6a08d49e6a13f2944d066067c
Source dataset
uspto-grants-2005_05
Patent number
US06897232B2

Reaction notes

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