Sodium Hydroxide → HCID 67267316, compound

HRID 598089Notes

Reaction equation

HRID 598089 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:5]=1[C:11]1[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-])=O)[C:12]=1[C:13]([NH:15][CH3:16])=[O:14]>O.CO.[Zn]>[CH3:3][C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:5]=1[C:11]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:12]=1[C:13](=[O:14])[N:15]([CH3:16])[NH:21]2

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 67267332HCID 67267332, compound

Product 1

HCID 67267316HCID 67267316, compoundYield 22%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of sodium hydroxide (0.035 g, 0.88 mmol) in water (2 ml) was added to a solution containing 0.095 g (0.33 mmol) of 2-(2,4-dimethylphenyl)-N-methyl-6-nitrobenzamide in methanol (1.5 ml). Zinc powder (0.03 g, 0.44 mmol) was then added to the mixture, which was heated under reflux for 24 h. After cooling, the zinc residue was separated by filtration and the methanol was partially evaporated. The residual solution was then adjusted to pH 7 with aqueous hydrochloric acid. The mixture was diluted with ethyl acetate and washed with saturated sodium bicarbonate. The organic phase was dried over magnesium sulfate. Filtration, removal of solvent and purification of the residue via biotage eluting with 40% ethyl acetate/hexanes gave 0.01 g (22%) of product.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 h
  3. temperatureAfter cooling
  4. customthe zinc residue was separated by filtration
  5. customthe methanol was partially evaporated
  6. additionThe mixture was diluted with ethyl acetate
  7. washwashed with saturated sodium bicarbonate
  8. dry with materialThe organic phase was dried over magnesium sulfate
  9. filtrationFiltration, removal of solvent and purification of the residue via biotage
  10. washeluting with 40% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-c6c45297501b4fab9b3d5adc17050edb
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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