Naphthalene → Ammonia

HRID 1829180Notes

Reaction equation

HRID 1829180 reaction equation
[Na].[CH:2]1[C:11]2[C:6](=CC=C[CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[O:12]1[CH2:17][CH2:16][CH:15]([CH:18]2[CH2:21][N:20]([S:22](OC3C=CC(C)=CC=3)(=[O:24])=[O:23])[CH2:19]2)[CH2:14][CH2:13]1>COCCOC>[NH3:20].[C:11]1([CH3:10])[CH:6]=[CH:5][C:4]([S:22]([OH:24])=[O:23])=[CH:3][CH:2]=1.[O:12]1[CH2:17][CH2:16][CH:15]([CH:18]2[CH2:21][NH:20][CH2:19]2)[CH2:14][CH2:13]1

Participants

6

Reactant 3

HCID 931NaphthaleneHCID 5360545SodiumHCID 22061289HCID 22061289, compound

Product 2

HCID 222AmmoniaHCID 22061307HCID 22061307, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

Sodium (390 mg, 16.6 mmol) was added to a solution of naphthalene (2.61 g, 20.4 mmol) in 1,2-dimethoxyethane (25 ml), and the solution stirred at room temperature for 4 hours. This solution was then added dropwise to a cooled (−70° C.) solution of 4-methylphenyl 3-tetrahydro-2H-pyran-4-yl-1-azetidinesulfonate (EP 962457) (1 g, 3.39 mmol) in 1,2-dimethoxyethane (25 ml), and once the addition was complete, the mixture was stirred at −70° C. for 20 minutes. The reaction was allowed to warm to room temperature, the reaction quenched by the addition of water and concentrated under reduced pressure. The residual gum was purified by column chromatography on silica gel using dichloromethane:methanol:0.88 ammonia (80:20:3) as eluant to give the title compound as an off-white gum, 690 mg.

Workup

  1. additionThis solution was then added dropwise to
  2. additiononce the addition
  3. stirringthe mixture was stirred at −70° C. for 20 minutes
  4. temperatureto warm to room temperature
  5. customthe reaction quenched by the addition of water
  6. concentrationconcentrated under reduced pressure
  7. customThe residual gum was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-2494ca5a4be14c54bbf62918fcfc63aa
Source dataset
uspto-grants-2006_06
Patent number
US07060836B2

Reaction notes

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