Water → 1-Cyclopropyl-4-nitronaphthalene

HRID 551343Notes

Reaction equation

HRID 551343 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>CCOC(C)=O>[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-cyclopropyl-naphthalene (6.4 g, 38 mmol) stirred at 0° C. The reaction mixture was stirred at 0° C. for an extra 30 min and then was slowly poured into ice. Water was added, followed by EtOAc. After extraction, the organic layer was washed with a 1% aqueous solution of NaOH, then washed with water, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography to yield 1-cyclopropyl-4-nitro-naphthalene (5.2 g, 64%).

Workup

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

Sources & evidence

ORD record
ord-32bed45292924b46a6f655557e85c95e
Source dataset
uspto-grants-2011_05
Patent number
US07947721B2

Reaction notes

Loading…