Sulfuric Acid → HCID 66882333, compound

HRID 1968720Notes

Reaction equation

HRID 1968720 reaction equation
[Cl:1][C:2]1[C:3]([CH2:13][C:14](Cl)(Cl)Cl)=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([CH3:12])=[CH:5]2.C[O-:19].[Na+].OS(O)(=O)=O.[C:26]([O-])(O)=[O:27].[Na+]>CO>[CH3:26][O:27][C:14](=[O:19])[CH2:13][C:3]1[C:2]([Cl:1])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[C:6]([CH3:12])[CH:7]=[N:8]2

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 10942334Sodium MethoxideHCID 668823716-Chloro-3-methyl-5-(2,2,2-trichloroethyl)quinoline

Product 1

HCID 66882333HCID 66882333, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
70 °C

Procedure

To a solution of 6-chloro-3-methyl-5-(2,2,2-trichloro-ethyl)quinoline (4.11 g, 13.3 mmol) in anhydrous methanol (35 mL) was added a 30% solution of NaOMe in methanol (10.7 mL) under an argon atmosphere. The resulting brown solution was heated for 4 h at 70° C. After cooling to 0° C., concentrated H2SO4 (7 mL) was carefully added and the resulting reaction mixture was heated for 1 h at 70° C. After cooling the reaction mixture was rendered basic (pH=9) with a saturated aqueous NaHCO3 solution and extracted three times with TBDM. The combined organic layers were dried over Na2SO4, filtered and concentrated at reduced pressure to afford a brown solid. Purification by flash column chromatography (silica gel, gradient of cyclohexane/EtOAc 100:0 to 80:20) afforded the title compound as a white powder (2.22 g, 8.90 mmol, 67%). 1H NMR (400 MHz, CDCl3, 298 K): δ=8.80 (s, 1H), 8.09 (s, 1H), 8.05 (d, J=9.2 Hz, 1H), 7.69 (d, J=9.2 Hz, 1H), 4.29 (s, 2H), 3.73 (s, 3H), 2.59 (s, 3H). MS (ES+): 250 (M(C13H1235ClNO2)+H)+.

Workup

  1. temperatureAfter cooling to 0° C.
  2. customthe resulting reaction mixture
  3. temperaturewas heated for 1 h at 70° C
  4. temperatureAfter cooling the reaction mixture
  5. extractionextracted three times with TBDM
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated at reduced pressure
  9. customto afford a brown solid
  10. customPurification by flash column chromatography (silica gel, gradient of cyclohexane/EtOAc 100:0 to 80:20)

Sources & evidence

ORD record
ord-748614bb07f9457eb7a1681281749ba6
Source dataset
uspto-grants-2013_04
Patent number
US08426440B2

Reaction notes

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