Sodium Hydroxide → HCID 68195302, compound

HRID 70818Notes

Reaction equation

HRID 70818 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[C:12]1[C:17](C)=[CH:16][CH:15]=[CH:14][N:13]=1.Cl[C:20]1C=CC=C(C(OO)=O)C=1.[OH-:30].[Na+]>ClCCl>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([CH3:20])=[CH:14][N+:13]=1[O-:30]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 681950842-(2-Chloronaphthalen-1-yl)-3-methylpyridine

Product 1

HCID 68195302HCID 68195302, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A round-bottomed flask having a volume of 50 mL and equipped with a glass stopper and a three-way cock was dried, and 890 mg (3.51 mmol) of 2-(2-chloronaphthalen-1-yl)-3-methylpyridine and 20 mL of dichloromethane were introduced thereinto. This colorless solution was cooled to 0° C., and then 1.59 g (69-75%) of m-CPBA (meta-chloroperbenzoic acid) was each added thereto three times at intervals of 10 minutes. Next, the temperature was slowly increased to room temperature, and the colorless solution was stirred for 2 hours. Thereafter, the solution was cooled to 0° C. again, and 10 mL of an aqueous NaOH solution having a concentration of 1M was gradually added. Thereafter, an organic layer was washed with 10 mL of an aqueous NaOH solution having a concentration of 1M and 10 mL of salt water, then dried with 50 g of sodium sulfate, and subjected to dehydration and filtration steps, thereby obtaining 947 mg of yellow oily 2-(2-chloronaphthalen-1-yl)-5-methylpyridine-1-oxide.

Workup

  1. customA round-bottomed flask having
  2. customa volume of 50 mL and equipped with a glass stopper
  3. customa three-way cock was dried
  4. additioneach added
  5. customat intervals of 10 minutes
  6. temperatureNext, the temperature was slowly increased to room temperature
  7. temperatureThereafter, the solution was cooled to 0° C. again
  8. additionwas gradually added
  9. washThereafter, an organic layer was washed with 10 mL of an aqueous NaOH solution
  10. dry with materialdried with 50 g of sodium sulfate
  11. filtrationsubjected to dehydration and filtration steps

Sources & evidence

ORD record
ord-ccbb045796ad4830ad7db75f7ccfe1b5
Source dataset
uspto-grants-2014_09
Patent number
US08822696B2

Reaction notes

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