m-Chloroperbenzoic acid → HCID 70224223, compound

HRID 1384263Notes

Reaction equation

HRID 1384263 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:5]2=[CH:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].ClC1C=CC=C(C(OO)=[O:26])C=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:1][C:2]1[N+:7]([O-:26])=[C:6]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:5]2=[CH:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 21186750HCID 21186750, compound

Product 1

HCID 70224223HCID 70224223, compoundYield 74.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In an atmosphere of argon, ethyl 2-methyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carboxylate (13.50 g, 57.9 mmol) was dissolved in methylene chloride (300.0 ml) to which was subsequently added metachloroperbenzoic acid (87.9%, 14.79 g, 75.3 mmol) in small portions at 0° C., and the resulting mixture was stirred at the same temperature for 2 hours and then at room temperature for 10 hours. The reaction solution was mixed with saturated sodium bicarbonate aqueous solution at 0° C. and extracted with methylene chloride, and the thus obtained organic layer was washed with saturated sodium bicarbonate aqueous solution, water and saturated brine in that order and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by a silica gel column chromatography (ethyl acetate:hexane=5:1—ethyl acetate) to obtain the title compound (10.80 g, 74.9%) as white powder.

Workup

  1. customat 0° C.
  2. waitat room temperature for 10 hours
  3. extractionextracted with methylene chloride
  4. washthe thus obtained organic layer was washed with saturated sodium bicarbonate aqueous solution, water and saturated brine in that order
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe resulting residue was purified by a silica gel column chromatography (ethyl acetate:hexane=5:1—ethyl acetate)

Sources & evidence

ORD record
ord-dd3fb7168af248b5b2570d48c5376aaa
Source dataset
uspto-grants-2001_07
Patent number
US06258829B1

Reaction notes

Loading…