Sodium Hydroxide → HCID 58574265, compound

HRID 1619300Notes

Reaction equation

HRID 1619300 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][CH3:9])=[O:7])=[C:4]([NH:12][C:13](=O)[CH2:14][CH2:15][O:16][CH3:17])[CH:3]=1.[OH-].[Na+].O1CCOCC1>O>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([C:6](=[O:7])[N:8]([CH3:9])[C:13]([CH2:14][CH2:15][O:16][CH3:17])=[N:12]2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 67257981HCID 67257981, compound

Product 1

HCID 58574265HCID 58574265, compoundYield 124.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The mixture of 4-bromo-2-(3-methoxypropanamido)-N-methylbenzamide (0.05 g, 0.159 mmol), 2.5 N NaOH (1 mL) and dioxane (1 mL) was stirred for 3 h at room temperature, then diluted with water, and extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with brine (3×10 mL), dried over Na2SO4, filtered, and evaporated to give 59 mg of the target compound. MS (ESI): 297, 299 (MH+).

Workup

  1. extractionextracted with ethyl acetate (3×10 mL)
  2. washThe combined organic layers were washed with brine (3×10 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-726eb60277be404d8be9f9ceb1316b21
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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