Sodium Hydroxide → 3-(4-Amino-1-naphthyl)propanoic acid

HRID 488668Notes

Reaction equation

HRID 488668 reaction equation
C[O:2][C:3](=[O:17])[CH:4]=[CH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([NH2:16])=[CH:8][CH:7]=1.[OH-].[Na+]>CO.[Pd]>[NH2:16][C:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:6]([CH2:5][CH2:4][C:3]([OH:17])=[O:2])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 69800264HCID 69800264, compound

Product 1

HCID 222719303-(4-Amino-1-naphthyl)propanoic acidYield 101.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 3-(4-amino-naphthalen-1-yl)-acrylic acid methyl ester (2.5 g, 11.0 mmol) and 10% Pd—C (320 mg) in methanol (100 mL) under an atmosphere of H2 for 18 hours then filtered. To the filtrate was added 19M NaOH (3 mL), and the resulting mixture heated to reflux for 30 minutes. The mixture was concentrated under reduced pressure taken up in water (10 mL) and the pH adjust to 4 with 12M HCl. The mixture was extracted with ethyl acetate (3×20 mL), then the combined ethyl acetate layers were washed with brine (1×10 mL), dried (MgSO4), filtered, and concentrated under reduced pressure to provide the titled compound (2.4 g, 100%).

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureto reflux for 30 minutes
  3. concentrationThe mixture was concentrated under reduced pressure
  4. extractionThe mixture was extracted with ethyl acetate (3×20 mL)
  5. washthe combined ethyl acetate layers were washed with brine (1×10 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4560413960274d1ba405b3438329719d
Source dataset
uspto-grants-2005_12
Patent number
US06972340B2

Reaction notes

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