Hydrogen Peroxide → 3-Chloro-6,7-dihydro-5h-cyclopenta[b]pyridine 1-oxide

HRID 1626128Notes

Reaction equation

HRID 1626128 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[CH2:6][CH2:7][CH2:8][C:9]=2[CH:10]=1.[OH:11]O>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[N+:4]([O-:11])[C:5]2[CH2:6][CH2:7][CH2:8][C:9]=2[CH:10]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 681078143-Chloro-6,7-dihydro-5H-cyclopenta[b]pyridine

Product 1

HCID 580828393-Chloro-6,7-dihydro-5h-cyclopenta[b]pyridine 1-oxide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 3-chloro-6,7-dihydro-5H-[1]pyrindine (3.03 g, 19.7 mmol) in acetic acid (19.7 ml) was treated at room temperature with hydrogen peroxide (3.45 ml, 39.5 mmol). The mixture was heated to 70° C. and stirred at this temperature overnight. After completion, the reaction mixture was allowed to cool and was concentrated at reduced pressure. Water was added and the mixture was evaporated again. This procedure was repeated another 2 times. The residue was dissolved in ethyl acetate, washed with a saturated aqueous solution of sodium hydrogen carbonate and brine, then dried over sodium sulfate and evaporated at reduced pressure. The crude 3-chloro-6,7-dihydro-5H-[1]pyrindine 1-oxide was obtained as dark green crystals (2.07 g, 62% yield). MS (ISP): m/z=170 [M+H]+.

Workup

  1. temperatureto cool
  2. concentrationwas concentrated at reduced pressure
  3. additionWater was added
  4. customthe mixture was evaporated again
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with a saturated aqueous solution of sodium hydrogen carbonate and brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-4561bdeb29454057a1d134c42821bee4
Source dataset
uspto-grants-2014_07
Patent number
US08785436B2

Reaction notes

Loading…