Dichloromethane → HCID 22254567, compound

HRID 1611698Notes

Reaction equation

HRID 1611698 reaction equation
[CH2:1]([Cl:3])Cl.[CH3:4][CH:5]([O:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[N:20]=C[CH:18]=[CH:17]2)[CH2:6][C:7]([CH3:10])([CH3:9])[CH3:8].C1C=C(Cl)C=C(C(OO)=O)C=1>CCOC(C)=O>[Cl:3][C:1]1[CH:18]=[CH:17][C:16]2[C:21](=[C:12]([O:11][CH:5]([CH3:4])[CH2:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH:13]=[CH:14][CH:15]=2)[N:20]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 222545478-(1,3,3-Trimethylbutoxy)quinoline

Product 1

HCID 22254567HCID 22254567, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 100 mL round bottom flask charged with 2 mL of CH2Cl2, 0.500 g (2.07 mmol) of 8-(1,3,3-trimethylbutoxy)quinoline was slowly added with gentle heating in order to dissolve the material. To this was added 1.8 equiv m-CPBA (50–70% by weight) in three portions. After stirring for 30 min, the dense solution became a brown solid. The solid was dissolved in 25 mL EtOAc and the resulting solution was washed with 10% aqueous NaHSO3, saturated aqueous NaHCO3, and the organic layer evaporated in vacuo. After co-evaporation with toluene, the residue was dissolved in POCl3 (5 mL) and the flask fitted with a reflux condenser. The reaction flask was then placed in an oil bath that had been preheated to 95° C. for 15 min. After cooling to room temperature, the solution was concentrated down to a red oil, which was then dissolved in CH2Cl2 and washed with saturated aqueous NaHCO3 until the aqueous layers became basic. The organic layer was evaporated in vacuo and the residue was purified by silica gel column chromatography (EtOAc/hexanes) to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.37 (d, 1H), 7.55 (m, 3H), 7.34 (m, 1H), 4.70–4.93 (m, 1H), 1.90 (dd, 1H), 1.53 (dd, 1H), 1.30 (d, 3H), 0.94 (s, 9H); MS (DCI/NH3) m/z 277 [M+H]+.

Workup

  1. additionwas slowly added
  2. temperaturewith gentle heating in order
  3. dissolutionto dissolve the material
  4. washthe resulting solution was washed with 10% aqueous NaHSO3, saturated aqueous NaHCO3
  5. customthe organic layer evaporated in vacuo
  6. dissolutionAfter co-evaporation with toluene, the residue was dissolved in POCl3 (5 mL)
  7. customthe flask fitted with a reflux condenser
  8. customThe reaction flask was then placed in an oil bath
  9. waitthat had been preheated to 95° C. for 15 min
  10. concentrationthe solution was concentrated down to a red oil, which
  11. dissolutionwas then dissolved in CH2Cl2
  12. washwashed with saturated aqueous NaHCO3 until the aqueous layers
  13. customThe organic layer was evaporated in vacuo
  14. customthe residue was purified by silica gel column chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-de5609766032418db73d3dae0444fde4
Source dataset
uspto-grants-2006_01
Patent number
US06989392B2

Reaction notes

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