2-Aminopropanol → HCID 58629086, compound

HRID 1678056Notes

Reaction equation

HRID 1678056 reaction equation
[H-].[Na+].[NH2:3][CH:4]([CH3:7])[CH2:5][OH:6].[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11](Cl)[N:10]=1>C1COCC1>[Cl:8][C:9]1[N:10]=[C:11]([O:6][CH2:5][CH:4]([NH2:3])[CH3:7])[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 51262-AminopropanolHCID 169892,6-DichloropyridineHCID 24758Sodium hydride

Product 1

HCID 58629086HCID 58629086, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60 wt. percent oil dispersion, 560 mg, 14 mmol) was added to a stirred solution of 2-aminopropanol (1.2 mL, 14 mmol) in THF (25 mL). After 30 minutes, 2,6-dichloropyridine (2.0 g, 14 mmol) was added and the reaction heated at reflux for 8 hours. After cooling, the reaction was quenched with aqueous 1N hydrochloric acid and washed with ether (3×30 mL). The pH of the aqueous phase was then raised to 10-11 with 50 wt. percent aqueous sodium hydroxide and extracted with ether (3×50 mL). The organics were dried (MgSO4), filtered and solvent removed in vacuo leaving 2.2 g of a yellow oil.

Workup

  1. temperaturethe reaction heated
  2. temperatureat reflux for 8 hours
  3. temperatureAfter cooling
  4. customthe reaction was quenched with aqueous 1N hydrochloric acid
  5. washwashed with ether (3×30 mL)
  6. temperatureThe pH of the aqueous phase was then raised to 10-11 with 50 wt. percent aqueous sodium hydroxide
  7. extractionextracted with ether (3×50 mL)
  8. dry with materialThe organics were dried (MgSO4)
  9. filtrationfiltered
  10. customsolvent removed in vacuo

Sources & evidence

ORD record
ord-03a3886f4a034ca89ad710ad2487fe3b
Source dataset
uspto-grants-2011_08
Patent number
US08008487B2

Reaction notes

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