Potassium Carbonate → N-(3-propoxynaphthalen-2-yl)acetamide

HRID 1874019Notes

Reaction equation

HRID 1874019 reaction equation
[OH:1][C:2]1[C:3]([NH:12][C:13](=[O:15])[CH3:14])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.I[CH2:17][CH2:18][CH3:19].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:17]([O:1][C:2]1[C:3]([NH:12][C:13](=[O:15])[CH3:14])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 15881733N-(3-hydroxynaphthalen-2-yl)acetamide

Product 1

HCID 58492454N-(3-propoxynaphthalen-2-yl)acetamideYield 96%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-(3-Hydroxynaphthalen-2-yl)acetamide (4.87 g, 24.2 mmol) was suspended in acetonitrile (50 ml). A 1-iodopropane (4.52 g, 26.6 mmol) acetonitrile solution (40 ml) and potassium carbonate (4.35 g, 31.5 mmol) were added thereto, and the resulting mixture was stirred for 3 hours while heating under reflux. The mixture was then cooled to room temperature and concentrated to dryness under reduced pressure. Water was added to the residue, followed by extraction using dichloromethane. The thus-obtained organic layer was concentrated to dryness under reduced pressure, and the residue was then purified using silica gel column chromatography (dichloromethane:ethyl acetate=20:1). The purified product was concentrated to dryness under reduced pressure, giving a white powder of N-(3-propoxynaphthalen-2-yl)acetamide (5.64 g, yield: 96%).

Workup

  1. temperaturewhile heating
  2. temperatureunder reflux
  3. concentrationconcentrated to dryness under reduced pressure
  4. additionWater was added to the residue
  5. extractionfollowed by extraction
  6. concentrationThe thus-obtained organic layer was concentrated to dryness under reduced pressure
  7. customthe residue was then purified
  8. concentrationThe purified product was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-9dd1381357ba482da802ad439286e03b
Source dataset
uspto-grants-2012_11
Patent number
US08304546B2

Reaction notes

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