Hydrochloric Acid → 4-Ethylamino-3-pyridinol N,N-diethylcarbamate

HRID 399406Notes

Reaction equation

HRID 399406 reaction equation
[CH2:1]([N:3]([CH2:17][CH3:18])[C:4]([O:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][C:12]=1[NH:13][C:14](=O)[CH3:15])=[O:5])[CH3:2].B.CSC.Cl.N.O>O1CCCC1>[CH2:17]([N:3]([CH2:1][CH3:2])[C:4]([O:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][C:12]=1[NH:13][CH2:14][CH3:15])=[O:5])[CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 12423031(Dimethyl sulfide)trihydroboronHCID 12896473Azane;hydrateHCID 543912254-Acetylamino-3-pyridinol N,N-diethylcarbamate

Product 1

HCID 540063134-Ethylamino-3-pyridinol N,N-diethylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Acetylamino-3-pyridinol N,N-diethylcarbamate (3.43 g) was dissolved in tetrahydrofuran (75 mL) and then the reaction mixture was chilled in an ice-water bath. Borane/methyl sulfide (BMS) was added (3.25 mL, 2.60 g) and the reaction mixture was stirred in the cold bath for 30 minutes. At the end of this time an additional 3.0 mL of BMS was added and stirring was continued for 3 hours. The reaction mixture was then poured into ice/conc. HCl, stirred for 30 minutes, basified with NH3 /water and then extracted with ethyl acetate. The organic phase was then dried, concentrated and purified by flash chromatography to give 0.86 g of chromatographically pure product. This product was combined with a crop obtained from another run and recrystallized from hexane to give an analytically pure material, mp. 107°-108° C.

Workup

  1. temperaturethe reaction mixture was chilled in an ice-water bath
  2. additionAt the end of this time an additional 3.0 mL of BMS was added
  3. stirringstirring
  4. waitwas continued for 3 hours
  5. additionThe reaction mixture was then poured into ice/conc
  6. extractionextracted with ethyl acetate
  7. customThe organic phase was then dried
  8. concentrationconcentrated
  9. custompurified by flash chromatography
  10. customto give 0.86 g of chromatographically pure product
  11. customobtained from another run
  12. customrecrystallized from hexane
  13. customto give an analytically pure material, mp. 107°-108° C.

Sources & evidence

ORD record
ord-a78e904f4d1f41f2b8900cabb37f84ed
Source dataset
uspto-grants-1998_10
Patent number
US05821239

Reaction notes

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