HCID 58424985, compound → Ethyl 3-amino-5-methoxybenzoate

HRID 2409447Notes

Reaction equation

HRID 2409447 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[C:12]([N+:14]([O-])=O)[CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7].[H][H]>C(OCC)(=O)C.[Pd]>[NH2:14][C:12]1[CH:11]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

5

Reactant 2

HCID 58424985HCID 58424985, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58424907Ethyl 3-amino-5-methoxybenzoateYield 96.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The compound (5.1 g, 23.1 mmol) prepared in step 2 was dissolved in ethyl acetate (50.0 ml), added with 10%-palladium (Pd) (100 mg). The resulting mixture was then stirred at room temperature for 24 hours in presence of hydrogen gas. After completion, 10%-palladium (Pd) was removed by celite-filter and the filtrate concentrated to dryness. The residue was purified by flash column chromatography (hexane:ethyl acetate=2:1) to obtain the title compound (4.36 g, yield: 96.8%, white solid).

Workup

  1. customAfter completion, 10%-palladium (Pd) was removed
  2. filtrationby celite-filter
  3. concentrationthe filtrate concentrated to dryness
  4. customThe residue was purified by flash column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-0b8b5abadc8b4decabf1467fd024c965
Source dataset
uspto-grants-2014_08
Patent number
US08815891B2

Reaction notes

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