Sodium Hydroxide → 3-(3-Amino-4-isopropyl-phenyl)-5,5-dimethyl-1-pyridin-4-ylmethyl-imidazolidine-2,4-dione

HRID 2356941Notes

Reaction equation

HRID 2356941 reaction equation
[CH3:1][C:2]1([CH3:28])[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[C:5](=[O:14])[N:4]([C:15]2[CH:20]=[CH:19][C:18]([CH:21]([CH3:23])[CH3:22])=[C:17]([N+:24]([O-])=O)[CH:16]=2)[C:3]1=[O:27].[OH-].[Na+]>C(O)(=O)C.O.[Zn]>[NH2:24][C:17]1[CH:16]=[C:15]([N:4]2[C:3](=[O:27])[C:2]([CH3:1])([CH3:28])[N:6]([CH2:7][C:8]3[CH:9]=[CH:10][N:11]=[CH:12][CH:13]=3)[C:5]2=[O:14])[CH:20]=[CH:19][C:18]=1[CH:21]([CH3:22])[CH3:23]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 116609365,5-Dimethyl-3-(3-nitro-4-isopropylphenyl)-1-pyridin-4-ylmethyl-imidazolidine-2,4-dione

Product 1

HCID 115304483-(3-Amino-4-isopropyl-phenyl)-5,5-dimethyl-1-pyridin-4-ylmethyl-imidazolidine-2,4-dioneYield 62.9%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

2.64 g (6.90 mmol ) 5,5-dimethyl-3-(3-nitro-4-isopropyl-phenyl)-1-pyridin-4-ylmethyl-imidazolidine-2,4-dione were dissolved in 50 ml acetic acid. 7.22 g zinc dust were added in portions while temperature was kept below 45° C. The mixture was stirred for 1 h at RT, then diluted with 100 ml water, made alkaline with 6N sodium hydroxide solution and extracted with methylene chloride. Separating zinc salts were removed by filtration over cellite. Evaporation of the combined organic phases yielded 1.53 g product that were used without further purification.

Workup

  1. customwas kept below 45° C
  2. extractionextracted with methylene chloride
  3. customSeparating zinc salts were removed by filtration over cellite
  4. customEvaporation of the combined organic phases

Sources & evidence

ORD record
ord-127fa993296d4e84bf2982700c4bc42f
Source dataset
uspto-grants-2010_07
Patent number
US07759379B2

Reaction notes

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