Hydrochloric Acid → 3-Propoxynaphthalen-2-ylamine

HRID 2047965Notes

Reaction equation

HRID 2047965 reaction equation
[CH2:1]([O:4][C:5]1[C:6]([NH:15]C(=O)C)=[CH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:2][CH3:3].Cl.[OH-].[Na+]>C(O)C>[CH2:1]([O:4][C:5]1[C:6]([NH2:15])=[CH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58492454N-(3-propoxynaphthalen-2-yl)acetamide

Product 1

HCID 212799043-Propoxynaphthalen-2-ylamineYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-(3-Propoxynaphthalen-2-yl)acetamide (2.5 g, 10.2 mmol) was dissolved in ethanol (10 ml). Concentrated hydrochloric acid (5.2 ml) was added thereto, and the resulting mixture was stirred for 4 hours while heating under reflux. The reaction mixture was cooled to room temperature, and a 5N aqueous sodium hydroxide solution (12.5 ml) was added thereto to adjust its pH to 11, 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). The purified product was concentrated to dryness under reduced pressure, giving a white powder of 3-propoxynaphthalen-2-ylamine (2.05 g, yield: 100%).

Workup

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

Sources & evidence

ORD record
ord-72f59b43e4854346b2094ef0dab04602
Source dataset
uspto-grants-2013_11
Patent number
US08592593B2

Reaction notes

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