m-Chloroperbenzoic acid → HCID 86663636, compound

HRID 1777194Notes

Reaction equation

HRID 1777194 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][CH:5]([OH:12])[C:4]=2[N:3]=1.ClC1C=CC=C(C(OO)=[O:21])C=1>ClCCl>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][CH:5]([OH:12])[C:4]=2[N+:3]=1[O-:21]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 453787102-Chloro-5,6,7,8-tetrahydroquinolin-8-ol

Product 1

HCID 86663636HCID 86663636, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cold solution of 2-chloro-5,6,7,8-tetrahydroquinolin-8-ol (300 mg, 1.634 mmol) in dichloromethane (5 mL) was added 3-chloroperbenzoic acid (604 mg, 2.451 mmol) in small portions over a period of 5 min. The reaction mixture was slowly warmed to RT and stirred for 20 h. The reaction was quenched by the addition of water. The aqueous phase was removed and the organic layer was washed with a 10% aqueous sodium thiosulfate solution (2×), with a 2M sodium carbonate solution (2×), and with brine (1×). The organic layer was dried over sodium sulfate, filtered, and evaporated to dryness furnishing a beige solid. Amount 320 mg. Yield 98%.

Workup

  1. customThe reaction was quenched by the addition of water
  2. customThe aqueous phase was removed
  3. washthe organic layer was washed with a 10% aqueous sodium thiosulfate solution (2×), with a 2M sodium carbonate solution (2×)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customfurnishing a beige solid

Sources & evidence

ORD record
ord-6b75b86e4ef843a5bdfd6bc8f6794506
Source dataset
uspto-grants-2016_02
Patent number
US09266855B2

Reaction notes

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