Water → 1-Cyclopropyl-4-nitronaphthalene

HRID 38747

Reaction equation

HRID 38747 reaction equation
[N:1]([O-:3])=[O:2].[Na+].[CH:5]1([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][CH:9]=2)[CH2:7][CH2:6]1.O>C(OCC)(=O)C>[CH:5]1([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([N+:1]([O-:3])=[O:2])=[CH:10][CH:9]=2)[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 962WaterHCID 146686931-CyclopropylnaphthaleneHCID 23668193Sodium Nitrite

Product 1

HCID 598130791-Cyclopropyl-4-nitronaphthaleneYield 64%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Sodium nitrite (30 mL) was slowly added (over 2 hours) to 1-cyclopropylnaphthalene (6.4 g, 38 mmol) stirred at 0° C. The reaction mixture was stirred at 0° C. for an extra 30 min and then slowly poured into ice. Water was added, followed by ethyl acetate. After extraction, the organic layer was washed with aqueous sodium hydroxide (1%) and water, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography to yield 1-cyclopropyl-4-nitronaphthalene (5.2 g, 64%).

Workup

  1. stirringThe reaction mixture was stirred at 0° C. for an extra 30 min
  2. additionslowly poured into ice
  3. extractionAfter extraction
  4. washthe organic layer was washed with aqueous sodium hydroxide (1%) and water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-1d9159ea1eae40d68873195f16b62d5e
Source dataset
uspto-grants-2013_09
Patent number
US08524754B2

Linked notes

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