Ethylene Glycol → HCID 12191680, compound

HRID 1620258Notes

Reaction equation

HRID 1620258 reaction equation
[Cl:1][C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:14][CH3:15])[CH:8]=2)[N:3]=1.[CH2:16](O)[CH2:17][OH:18].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:11]([CH:12]2[O:18][CH2:17][CH2:16][O:13]2)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:14][CH3:15])[CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 521998p-Toluenesulfonic acid monohydrateHCID 6890792-Chloro-6-methoxyquinoline-3-carbaldehyde

Product 1

HCID 12191680HCID 12191680, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2-chloro-6-methoxyquinoline-3-carbaldehyde (4.01 g, 18.10 mmol) in toluene (200 mL) in a 500 mL round-bottomed flask equipped with a magnetic stirrer under N2 was added ethylene glycol (1.20 mL, 21.52 mmol) followed by p-toluenesulfonic acid monohydrate (348 mg, 1.83 mmol). The mixture was stirred overnight under reflux using a Dean-Stark apparatus. After cooling to RT, the mixture was concentrated at 40° C. under vacuum, then the residue was diluted with saturated aqueous NaHCO3 solution (40 mL) before extraction with CH2Cl2 (100 mL). The organic phase was isolated, washed with brine (20 mL), dried over Na2SO4, filtered and concentrated at 40° C. under vacuum. Purification by column chromatography (SiO2, eluent cyclohexane:EtOAc=100:0 to 92:8 to 75:25) gave 2-chloro-3-(1,3-dioxolan-2-yl)-6-methoxyquinoline SMA 44002 as a white solid (4.39 g, 91% yield).

Workup

  1. temperatureunder reflux
  2. concentrationthe mixture was concentrated at 40° C. under vacuum
  3. additionthe residue was diluted with saturated aqueous NaHCO3 solution (40 mL) before extraction with CH2Cl2 (100 mL)
  4. customThe organic phase was isolated
  5. washwashed with brine (20 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated at 40° C. under vacuum
  9. customPurification by column chromatography (SiO2, eluent cyclohexane:EtOAc=100:0 to 92:8 to 75:25)

Sources & evidence

ORD record
ord-2dd658e434524d2aad651c72ed160680
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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