HCID 4110969, compound → HCID 18622559, compound

HRID 1862037Notes

Reaction equation

HRID 1862037 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:12]3[C:22](=[O:23])[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:13]=3[NH:14][N:15]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[BH4-].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:12]3[CH:22]([OH:23])[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:13]=3[NH:14][N:15]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 4110969HCID 4110969, compoundHCID 4311764Sodium borohydride

Product 1

HCID 18622559HCID 18622559, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-(3,4-dimethoxyphenyl)indeno[1,2-c]pyrazol-4(1H)-one (0.6 g) and sodium borohydride (0.16 g) in absolute ethanol (100 ml) was boiled under reflux for 5 hours. The reaction mixture was cooled and the ethanol removed under reduced pressure. Water (20 ml) was added and the mixture was extracted with ethyl acetate (3×50 ml). The combined ethyl acetate extracts were washed with water, dried, filtered and evaporated to give a solid which was purified by preparative high performance liquid chromatography on a Dynamax C18 reverse phase (41.4×250 mm) column using acetonitrile/triethylammonium formate buffer as eluant to give 3-(3,4-dimethoxyphenyl)-1,4-dihydroindeno[1,2-c]pyrazol-4-ol, m.p. 197-199° C.

Workup

  1. temperatureunder reflux for 5 hours
  2. temperatureThe reaction mixture was cooled
  3. customthe ethanol removed under reduced pressure
  4. additionWater (20 ml) was added
  5. extractionthe mixture was extracted with ethyl acetate (3×50 ml)
  6. washThe combined ethyl acetate extracts were washed with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customto give a solid which
  11. customwas purified by preparative high performance liquid chromatography on a Dynamax C18 reverse phase (41.4×250 mm) column

Sources & evidence

ORD record
ord-e02d70a12e2c4014a0c3336356f259b1
Source dataset
uspto-grants-2003_03
Patent number
US06534655B1

Reaction notes

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