m-Chloroperbenzoic acid → HCID 66637270, compound

HRID 1924792Notes

Reaction equation

HRID 1924792 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][CH:9]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:23])C=1>C(Cl)(Cl)Cl>[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N+:11]([O-:23])=[CH:10][CH:9]=[CH:8]2)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 1096386-tert-Butylquinoline

Product 1

HCID 66637270HCID 66637270, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 6-tert-butylquinoline (400 mg, 2.16 mmol, Journal of the Indian Chemical Society, 1998, 823), mCPBA (639 mg, 2.59 mmol) in chloroform (10 ml) was stirred for 2 hours at room temperature. The mixture was concentrated and the crude residue was applied to a silica gel (NH silica) column chromatography and eluted with DCM/MeOH (20:1) to furnish the title compound (433 mg, quant.) as pale orange oil. 1H NMR (300 MHz, CDCl3) δ 1.43 (9H, s) 7.26-7.30 (1H, m), 7.73 (1H, d, J=8.1 Hz), 7.78 (1H, s), 7.85 (1H, dd, J=1.5, 8.8 Hz), 8.49 (1H, d, J=5.9 Hz), 8.67 (1H, d, J=8.8 Hz) MS (ESI):m/z 202 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. washeluted with DCM/MeOH (20:1)

Sources & evidence

ORD record
ord-7e9f9267bab24d0f9a9422654dbb1df3
Source dataset
uspto-grants-2012_05
Patent number
US08178558B2

Reaction notes

Loading…