Potassium Iodide → 2-[[6-(Hydroxymethyl)-2-naphthyl]oxy]-2-methylpropanamide

HRID 585307Notes

Reaction equation

HRID 585307 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([OH:13])[CH:7]=[CH:6]2.[OH-].[Na+].Br[C:17]([CH3:22])([CH3:21])[C:18]([NH2:20])=[O:19].[I-].[K+]>CC(N(C)C)=O.O>[OH:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([O:13][C:17]([CH3:22])([CH3:21])[C:18]([NH2:20])=[O:19])[CH:7]=[CH:6]2

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 14798Sodium HydroxideHCID 1012352-Bromo-2-methylpropanamideHCID 113327606-(Hydroxymethyl)naphthalen-2-ol

Product 1

HCID 223405142-[[6-(Hydroxymethyl)-2-naphthyl]oxy]-2-methylpropanamideYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of 6-(hydroxymethyl)-2-naphthol (500 mg, 2.87 mmol) in dimethylacetamide (4 ml) was added sodium hydroxide (344 mg, 8.61 mmol), and the mixture was stirred for 1 hour. 2-bromo-2-methylpropanamide (1.43 g, 8.61 mmol) and potassium iodide (476 mg, 2.87 mmol) were added thereto, and the mixture was stirred at room temperature for 16 hours. To the reaction solution was added water, and the mixture was extracted with ethyl acetate. The extract was washed with a 1N aqueous sodium hydroxide solution and an aqueous saturated sodium chloride solution, and dried over anhydrous sodium sulfate. After the solvent was concentrated under reduced pressure, 2-[[6-(hydroxymethyl)-2-naphthyl]oxy]-2-methylpropanamide (506 mg) was obtained as a colorless powder from isopropyl ether.

Workup

  1. stirringthe mixture was stirred at room temperature for 16 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with a 1N aqueous sodium hydroxide solution
  4. dry with materialan aqueous saturated sodium chloride solution, and dried over anhydrous sodium sulfate
  5. concentrationAfter the solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9d12bf35e6df433c997d4cc02414a9b5
Source dataset
uspto-grants-2005_08
Patent number
US06930185B2

Reaction notes

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