Water → 1-Cyclopropyl-4-nitronaphthalene

HRID 1844258Notes

Reaction equation

HRID 1844258 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-29472300e7d1485e90f36a26f4769a4d
Source dataset
uspto-grants-2015_02
Patent number
US08946273B2

Reaction notes

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