Ethylene Glycol → HCID 50877440, compound

HRID 1878689Notes

Reaction equation

HRID 1878689 reaction equation
[Na].[CH2:2]([OH:5])[CH2:3][OH:4].Cl[C:7]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[N:10]=[CH:9][CH:8]=1>O>[CH3:18][O:17][C:13]1[CH:12]=[C:11]2[C:16]([C:7]([O:4][CH2:3][CH2:2][OH:5])=[CH:8][CH:9]=[N:10]2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 5360545SodiumHCID 106078294-Chloro-7-methoxyquinoline

Product 1

HCID 50877440HCID 50877440, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

In a 1 L RBF under nitrogen was placed sodium (15 g, 652 mmol) cubes. The flask was cooled in an ice bath and ethane-1,2-diol (150 ml, 2690 mmol) was added slowly through an addition funnel (15 min). The cooling bath was removed and the reaction mixture was allowed to warm to 50° C. until all the sodium disappeared. After 20 min, the mixture was heated to 110° C. and 4-chloro-7-methoxyquinoline (69 g, 356 mmol) was added. After 12 h, the mixture was cooled to room temperature and was diluted with H2O (250 mL), resulting the formation of a thick sludge. The content was filtered, and washed with H2O (2×50 mL). After air drying overnight, the solid was heated with benzene (300 mL) under reflux for 3 hr. The mixture was cooled and filtered. The solid was washed with ether (2×50 mL) to give a soft solid (77 g) contaminated with the small amount of bisether dimer. MS (ESI pos. ion) calcd for C12H13NO3: 219.2; found: 220.1 (MH+). 1H NMR (400 MHz, Chloroform-d) δ ppm 3.94 (s, 3H) 4.13 (t, 2H) 4.32 (t, 2H) 6.64 (d, J=5.28 Hz, 1H) 7.14 (dd, J=9.19, 2.54 Hz, 1H) 7.37 (d, J=2.35 Hz, 1H) 8.08 (d, J=9.19 Hz, 1H) 8.66 (d, J=5.48 Hz, 1H)

Workup

  1. temperatureThe flask was cooled in an ice bath
  2. customThe cooling bath was removed
  3. temperaturethe mixture was heated to 110° C.
  4. waitAfter 12 h
  5. temperaturethe mixture was cooled to room temperature
  6. customresulting the formation of a thick sludge
  7. filtrationThe content was filtered
  8. washwashed with H2O (2×50 mL)
  9. customAfter air drying overnight
  10. temperaturethe solid was heated with benzene (300 mL)
  11. temperatureunder reflux for 3 hr
  12. temperatureThe mixture was cooled
  13. filtrationfiltered
  14. washThe solid was washed with ether (2×50 mL)

Sources & evidence

ORD record
ord-654dd7b245944866a8326a1c325956d5
Source dataset
uspto-grants-2012_11
Patent number
US08314087B2

Reaction notes

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