Potassium Hydroxide → HCID 19805429, compound

HRID 1681689Notes

Reaction equation

HRID 1681689 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Br)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:12]([N:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19](=[O:26])[NH:18]1)([O:14][CH2:15][CH3:16])=[O:13].[OH-].[K+]>C(O)C>[C:12]([N:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19](=[O:26])[N:18]1[CH2:8][C:7]1[CH:10]=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 660114-Nitrobenzyl bromideHCID 584113Ethyl 3-oxo-2,3-dihydro-1H-indazole-1-carboxylate

Product 1

HCID 19805429HCID 19805429, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Nitrobenzyl bromide (540 mg) was added to a mixture of 1,2-dihydro-1-carboethoxy-3H-indazol-3-one (206 mg) and potassium hydroxide (67 mg) in ethanol (10 ml). The mixture was heated under reflux for 30 minutes. The cooled solution was clarified by filtration and the filtrate was evaporated. The residue was purified by column chromatography using methylene chloride as eluant to give 1,2-dihydro-1-carboethoxy-2-(4-nitrobenzyl)-3H-indazol-3-one (Ex. 39) as a solid, m.p. 123-124° C. in 59% yield.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 30 minutes
  3. filtrationThe cooled solution was clarified by filtration
  4. customthe filtrate was evaporated
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-b5a0debec6f14606927ce7535fbf838d
Source dataset
uspto-grants-1992_12
Patent number
US05173496

Reaction notes

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