Tetrahydrofuran → Ethyl 5-aminonaphthalene-1-carboxylate

HRID 1610191Notes

Reaction equation

HRID 1610191 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]([O:16][CH2:17][CH3:18])=[O:15])([O-])=O.O1CCCC1>C(O)C.[Pd]>[NH2:1][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 285289Ethyl 5-nitro-1-naphthoate

Product 1

HCID 22261675Ethyl 5-aminonaphthalene-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of ethyl 5-nitro-1-naphthoate (3.304 g, 13.47 mmol) in ethanol (10 ml)-tetrahydrofuran (20 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-721e4abc6c6846f6afcdb788475bc835
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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