Ethyl 3-nitro-1-naphthoate → Ethyl 3-aminonaphthalene-1-carboxylate

HRID 1610204Notes

Reaction equation

HRID 1610204 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

4

Reactant 1

HCID 22262323Ethyl 3-nitro-1-naphthoate

Product 1

HCID 22261680Ethyl 3-aminonaphthalene-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of ethyl 3-nitro-1-naphthoate (5.371 g, 21.90 mmol) in ethanol (30 ml) was hydrogenated under normal temperature and normal pressure using 10% palladium/carbon (containing water by 50%) (0.5 g) as a catalyst until the starting material disappeared. The catalyst was filtered off and the solvent was evaporated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (hexane/ethyl acetate=6/1−3/1) to give the objective substance.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent was evaporated under reduced pressure
  3. customThe obtained crude product
  4. customwas purified by silica gel column chromatography (hexane/ethyl acetate=6/1−3/1)
  5. customto give the objective substance

Sources & evidence

ORD record
ord-cb67d76bd3f0405ea8b3b9ef0956d607
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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