3-Bromoquinoline → 3-bromoquinoline 1-oxide

HRID 74497Notes

Reaction equation

HRID 74497 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Br:12][C:13]1[CH:14]=[N:15][C:16]2[C:21]([CH:22]=1)=[CH:20][CH:19]=[CH:18][CH:17]=2>C(Cl)Cl>[Br:12][C:13]1[CH:14]=[N+:15]([O-:9])[C:16]2[C:21]([CH:22]=1)=[CH:20][CH:19]=[CH:18][CH:17]=2

Participants

4

Reactant 2

HCID 214133-BromoquinolineHCID 70297m-Chloroperbenzoic acid2×

Product 1

HCID 8180763-bromoquinoline 1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
5 °C

Procedure

A solution of 72% 3-chloroperbenzoic acid (97.8 g (0.408 mol) dissolved in 1 L DCM, dried on sodium sulphate and filtered off) was added dropwise to a solution of 85.0 g 0.41 mol) 3-bromoquinoline in 100 mL DCM cooled to 5° C. Care was taken to ensure that the temperature of the reaction mixture did not rise above 10° C. After the addition had ended the mixture was stirred for 5 h, then a solution of 72% 3-chloroperbenzoic acid (25.0 g, 0.104 mol) dissolved in 200 mL DCM, dried on sodium sulphate and filtered off) was again added dropwise and the mixture was stirred overnight at RT. Saturated aqueous sodium carbonate solution was added, the phases were separated and the organic phase was dried on sodium sulphate. The solution was filtered through activated charcoal and then evaporated down i. vac.

Workup

  1. customdid not rise above 10° C
  2. additionAfter the addition
  3. customdried on sodium sulphate
  4. filtrationfiltered off)
  5. additionwas again added dropwise
  6. stirringthe mixture was stirred overnight at RT
  7. additionSaturated aqueous sodium carbonate solution was added
  8. customthe phases were separated
  9. customthe organic phase was dried on sodium sulphate
  10. filtrationThe solution was filtered through activated charcoal
  11. customevaporated down i

Sources & evidence

ORD record
ord-2ea77c6c7907431ab0cc0e6ec7971c72
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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