1-Cyclopropyl-4-nitronaphthalene → 4-Cyclopropylnaphthalen-1-amine

HRID 660452Notes

Reaction equation

HRID 660452 reaction equation
[CH:1]1([C:4]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]([N+:14]([O-])=O)=[CH:6][CH:5]=2)[CH2:3][CH2:2]1>C(O)C.[Pd]>[NH2:14][C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:4]([CH:1]2[CH2:3][CH2:2]2)=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 598130791-Cyclopropyl-4-nitronaphthalene

Product 1

HCID 534821124-Cyclopropylnaphthalen-1-amineYield 73.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-cyclopropyl-4-nitronaphthalene (5 g, 23 mmol) in ethanol (200 mL) was stirred under hydrogen in the presence of Pd/C (10% net, 10.8 g). The reaction mixture was shaken overnight, filtered over celite, and concentrated under reduced pressure. The residue was purified by silica gel chromatography to yield 1-amino-4-cyclopropylnaphthalene (3.1 g, 73%).

Workup

  1. filtrationfiltered over celite
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-e5640707c6ec4b03b35865faf59ea143
Source dataset
uspto-grants-2011_12
Patent number
US08084483B2

Reaction notes

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