Sodium Hydroxide → HCID 19805538, compound

HRID 1681690Notes

Reaction equation

HRID 1681690 reaction equation
[CH2:1]([NH:8][C:9](=[O:20])[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=1[N+:17]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+].[OH-].[Na+]>CO.O.[Zn]>[CH2:1]([N:8]1[C:9](=[O:20])[C:10]2[C:11](=[CH:12][C:13]([Cl:16])=[CH:14][CH:15]=2)[NH:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 517165Ammonium AcetateHCID 789173HCID 789173, compound

Product 1

HCID 19805538HCID 19805538, compoundYield 19.4%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

N-(Benzyl)-4-chloro-2-nitrobenzamide (obtained by reaction of benzylamine with 4-chloro-2-nitrobenzoyl chloride) (1.16 g) was dissolved in a mixture of methanol (20 ml) and water (4 ml). Zinc dust (520 mg) was then added in one portion. Ammonium acetate (1.23 g) was then added in portions to the rapidly stirred reaction mixture. After the addition was complete, 2M sodium hydroxide solution (8 ml) was added and the mixture was heated under reflux for 4 hours. The cooled mixture was then concentrated in vacuo to remove methanol and then acidified to pH6 with 2M hydrochloric acid. This mixture was extracted with ethyl acetate. The extracts were washed with brine, dried (MgSO4) and evaporated. The residue was purified by column chromatography using an increasing gradient of ether in methylene chloride to give 1,2-dihydro-2-benzyl-6-chloro-3H-indazol-3-one (Ex. 43) as a solid (0.2 g), m.p. 209-214° C.

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 4 hours
  4. concentrationThe cooled mixture was then concentrated in vacuo
  5. customto remove methanol
  6. extractionThis mixture was extracted with ethyl acetate
  7. washThe extracts were washed with brine
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-5411df1ba54b4bde871d4112834695bc
Source dataset
uspto-grants-1992_12
Patent number
US05173496

Reaction notes

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