Sodium Hydroxide → HCID 14898710, compound

HRID 1681684Notes

Reaction equation

HRID 1681684 reaction equation
[OH-].[Na+].[C:3]1([CH2:13][NH:14][C:15](=[O:25])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N+:22]([O-])=O)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1>O.CO.[Zn]>[C:3]1([CH2:13][N:14]2[C:15](=[O:25])[C:16]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:22]2)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 14898709HCID 14898709, compound

Product 1

HCID 14898710HCID 14898710, compoundYield 44.1%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of sodium hydroxide (4.13 g) in water (80 ml) was added to a solution of N-(1-naphthylmethyl)-2-nitrobenzamide (7.6 g) in methanol (60 ml). Zinc powder (3.35 g) was then added to the mixture which was heated under reflux for 24 hours. After cooling, the zinc residue was separated by filtration and the methanol was partially evaporated. The residual solution was then adjusted to pH7 with hydrochloric acid. The precipitated solid was collected, dried and purified by column chromatography, eluting with methylene chloride/ether/methanol (50/50/5 v/v) to give 1,2-dihydro-2-(1-naphthylmethyl)-3H-indazol-3-one (3.0 g), as a white solid after washing with acetone, m.p. 198-200° C. (acetone/ether).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. temperatureAfter cooling
  4. customthe zinc residue was separated by filtration
  5. customthe methanol was partially evaporated
  6. customThe precipitated solid was collected
  7. customdried
  8. custompurified by column chromatography
  9. washeluting with methylene chloride/ether/methanol (50/50/5 v/v)

Sources & evidence

ORD record
ord-87e9b03c77ac4c3eb4bfe8b95d85a95b
Source dataset
uspto-grants-1992_12
Patent number
US05173496

Reaction notes

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