Dimethylformamide → HCID 18415787, compound

HRID 990991Notes

Reaction equation

HRID 990991 reaction equation
[NH:1]1[C:5]2[C:6]3[C:11]([CH2:12][C:4]=2[C:3]([C:13]2[CH:14]=[C:15]([OH:19])[CH:16]=[CH:17][CH:18]=2)=[N:2]1)=[CH:10][CH:9]=[CH:8][CH:7]=3.C1(=O)O[CH2:23][CH2:22][O:21]1.[OH-].[Na+].CN(C)C=O>C(OCC)(=O)C>[NH:1]1[C:5]2[C:6]3[C:11]([CH2:12][C:4]=2[C:3]([C:13]2[CH:14]=[C:15]([CH:16]=[CH:17][CH:18]=2)[O:19][CH2:23][CH2:22][OH:21])=[N:2]1)=[CH:10][CH:9]=[CH:8][CH:7]=3

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7303Ethylene carbonateHCID 14798Sodium HydroxideHCID 9859735HCID 9859735, compound

Product 1

HCID 18415787HCID 18415787, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)phenol (0.29 g), ethylene carbonate (0.11 g), a trace of solid sodium hydroxide (spatula tip of 20-40 mesh beads) and dry dimethylformamide (3 ml) was stirred under nitrogen and heated at 100° C. for 45 minutes. The external temperature was raised to 140° C. and the mixture heated at this temperature for 3.5 hours. The reaction mixture was cooled and diluted with ethyl acetate and the mixture washed with dilute aqueous sodium hydroxide solution and then with water. The organic phase was dried, filtered and evaporated to give a residue which was purified by flash column chromatography on silica using ethyl acetate as the mobile phase. Appropriate fractions were collected, combined and evaporated to give a solid with was triturated with diethyl ether and filtered to give 2-[3-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)phenoxy]ethanol, m.p. 203-205° C.

Workup

  1. temperatureThe external temperature was raised to 140° C.
  2. temperaturethe mixture heated at this temperature for 3.5 hours
  3. temperatureThe reaction mixture was cooled
  4. washthe mixture washed with dilute aqueous sodium hydroxide solution
  5. customThe organic phase was dried
  6. filtrationfiltered
  7. customevaporated
  8. customto give a residue which
  9. customwas purified by flash column chromatography on silica
  10. customAppropriate fractions were collected
  11. customevaporated
  12. customto give a solid
  13. customwith was triturated with diethyl ether
  14. filtrationfiltered

Sources & evidence

ORD record
ord-57828d69a3444aec95375a6764d9a493
Source dataset
uspto-grants-2002_10
Patent number
US06462036B1

Reaction notes

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