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

HRID 1696483Notes

Reaction equation

HRID 1696483 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]([N+:16]([O-])=O)[CH:7]=1)=[O:5])[CH3:2]>CCO.[Pd]>[NH2:16][C:8]1[CH:7]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:15]2[C:10]([CH:9]=1)=[CH:11][CH:12]=[CH:13][CH:14]=2

Participants

4

Reactant 1

HCID 22262323Ethyl 3-nitro-1-naphthoate

Product 1

HCID 22261680Ethyl 3-aminonaphthalene-1-carboxylateYield 94.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-nitronaphthalene-1-carboxylic acid ethyl ester (2.45 g, 10 mmol) and Pd/C (0.3 g) in EtOH (20 mL) was stirred overnight at RT under 35 psi of H2. After filtration, the filtrate was concentrated to yield ethyl 3-aminonaphthalene-1-carboxylate (2.04 g). 1H NMR (300 MHz, DMSO-d6): δ 8.63 (m, 1H), 7.93-7.97 (m, 2H), 7.84 (s, 1H), 7.54-7.57 (m, 2H), 4.39 (q, J=7.2 Hz, 2H), 1.35 (t, J=7.2 Hz, 3H).

Workup

  1. filtrationAfter filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ce6ccad08fe348c9b868aa58139f0bab
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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