2,3-Dihydro-3-(hydroxyimino)-1H-indene-4-carboxylic acid → HCID 22136829, compound

HRID 1826995Notes

Reaction equation

HRID 1826995 reaction equation
O[N:2]=[C:3]1[C:11]2[C:10]([C:12]([OH:14])=[O:13])=[CH:9][CH:8]=[CH:7][C:6]=2[CH2:5][CH2:4]1>Cl.C(O)(=O)C.[Zn]>[NH2:2][CH:3]1[C:11]2[C:10]([C:12]([OH:14])=[O:13])=[CH:9][CH:8]=[CH:7][C:6]=2[CH2:5][CH2:4]1

Participants

5

Reactant 1

HCID 750891902,3-Dihydro-3-(hydroxyimino)-1H-indene-4-carboxylic acid

Product 1

HCID 22136829HCID 22136829, compoundYield 34.1%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of the 3-hydroxyimino-indan-4-carboxylic acid (0.45 g, 2.35 mmol), zinc powder (0.72 g) in 1M HCl (10 ml) and glacial acetic acid (3 ml) was heated to 90° C. for 18 hours. The mixture was cooled to room temperature, the solid filtered off and the solvent removed by evaporation under reduced pressure. The residue was diluted with water (5 ml) and extracted with dichloromethane (3×10 ml) and ethyl acetate (5 ml). The aqueous fraction was purified by ion-exchange column (DOWEX™ 50WX2-100) eluting with a solvent gradient of ammonia: water (5:95) to give the title compound (0.142 g, 34%) as a white solid.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationthe solid filtered off
  3. customthe solvent removed by evaporation under reduced pressure
  4. additionThe residue was diluted with water (5 ml)
  5. extractionextracted with dichloromethane (3×10 ml) and ethyl acetate (5 ml)
  6. customThe aqueous fraction was purified by ion-exchange column (DOWEX™ 50WX2-100)
  7. washeluting with a solvent gradient of ammonia: water (5:95)

Sources & evidence

ORD record
ord-99999e570a5a400e9cfa4b6f734d5db7
Source dataset
uspto-grants-2006_05
Patent number
US07053122B2

Reaction notes

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