Sodium Carbonate → HCID 136383554, compound

HRID 991011Notes

Reaction equation

HRID 991011 reaction equation
[NH:1]1[C:5]2[C:6]3[C:11]([CH2:12][C:4]=2[C:3]([C:13]2[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=2)=[N:2]1)=[CH:10][CH:9]=[CH:8][CH:7]=3.Cl.[NH2:22][OH:23].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[NH:1]1[C:5]2[C:6]3[C:11]([CH2:12][C:4]=2[C:3]([C:13]2[CH:20]=[CH:19][C:16]([C:17](=[N:22][OH:23])[NH2:18])=[CH:15][CH:14]=2)=[N:2]1)=[CH:10][CH:9]=[CH:8][CH:7]=3

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 18415934HCID 18415934, compound

Product 1

HCID 136383554HCID 136383554, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzonitrile (730 mg, Example 65), hydroxylamine hydrochloride (0.4 g), sodium carbonate (0.8 g) and ethanol (30 ml) was boiled under reflux for about 16 hours. The solvent was removed under reduced pressure at about 50° C. and the residue stirred with water (70 ml). The mixture was extracted with ethyl acetate and the combined organic phases dried, filtered and evaporated to give a solid. The solid was purified by flash column chromatography on silica using ethyl acetate as eluant to give a solid which was washed with diethyl ether and dried to give 4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzamide oxime, m.p.>300° C.

Workup

  1. temperatureunder reflux for about 16 hours
  2. customThe solvent was removed under reduced pressure at about 50° C.
  3. extractionThe mixture was extracted with ethyl acetate
  4. customthe combined organic phases dried
  5. filtrationfiltered
  6. customevaporated
  7. customto give a solid
  8. customThe solid was purified by flash column chromatography on silica
  9. customto give a solid which
  10. washwas washed with diethyl ether
  11. customdried

Sources & evidence

ORD record
ord-edf7b059057a4eb8b5979614a8830dd0
Source dataset
uspto-grants-2002_10
Patent number
US06462036B1

Reaction notes

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