Sodium Hydroxide → HCID 22408471, compound

HRID 439873Notes

Reaction equation

HRID 439873 reaction equation
Cl.[CH3:2][C:3]1[CH:4]=[C:5]([NH:13]N)[CH:6]=[C:7]([CH3:12])[C:8]=1[O:9][CH2:10][CH3:11].[CH3:15][CH:16]1[CH2:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]1=O.[OH-].[Na+]>C(O)(=O)C.O>[CH2:10]([O:9][C:8]1[C:3]([CH3:2])=[CH:4][C:5]2[N:13]=[C:17]3[C:18]4[C:23]([CH2:24][C:16]3([CH3:15])[C:6]=2[C:7]=1[CH3:12])=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH3:11]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 2492622-MethylindanoneHCID 22408536HCID 22408536, compound

Product 1

HCID 22408471HCID 22408471, compoundYield 96.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 2.16 g (0.01 mol) of 3,5-dimethyl-4-ethoxyphenylhydrazine hydrochloride and 1.46 g (0.01 mol) of 2-methyl-1-indanone in 20 ml of acetic acid was stirred overnight at room temperature and then refluxed for 3 hours. The mixture was diluted with water, alkalinized with 10N sodium hydroxide solution and extracted three times with methylene chloride. The combined organic phase was washed with water, dried (Na2SO4) and evaporated giving 2.8 g of crude product which was recrystallized from light petroleum/ethyl acetate (5/1). Yield 2.1 g (72%). M.p. 164° C.

Workup

  1. temperaturerefluxed for 3 hours
  2. extractionextracted three times with methylene chloride
  3. washThe combined organic phase was washed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-1f5e74ccf0e14e9bac91631ca5eb61e0
Source dataset
uspto-grants-1996_05
Patent number
US05516788

Reaction notes

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