Ethanol → HCID 178470772, compound

HRID 392622Notes

Reaction equation

HRID 392622 reaction equation
[N:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[NH:3][C:2]=1[CH2:10][C:11]#N.C([O-])(O)=[O:14].[Na+].[CH3:18][CH2:19][OH:20]>>[N:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[NH:3][C:2]=1[CH2:10][C:11]([O:20][CH2:19][CH3:18])=[O:14]

Participants

4

Reactant 3

HCID 702EthanolHCID 516892Sodium Bicarbonate2×HCID 178510881HCID 178510881, compound

Product 1

HCID 178470772HCID 178470772, compound

Conditions

Temperature
0 °C

Procedure

3H-Imidazo[4,5-b]pyridin-2-ylacetonitrile was suspended in EtOH, and gaseous HCl was bubbled through for 3 hours. The suspension initially seemed to dissolve, but a precipitate started forming almost immediately. The reaction mixture was cooled to 0° C. and a cold saturated NaHCO3 solution was carefully added. Solid NaHCO3 was also added to bring the pH to a value of 7.6. The aqueous phase was then extracted with EtOAc, and the organic extracts were dried (Na2SO4). After evaporation of the solvent under reduced pressure, the residue was purified by chromatography on silicagel (10% MeOH in CH2C2 with 1% Et3N) providing the desired product as a light brown solid. LC/MS m/z 206.1 (MH+), Rt 0.97 minutes.

Workup

  1. customgaseous HCl was bubbled through for 3 hours
  2. dissolutionto dissolve
  3. customa precipitate started forming almost immediately
  4. extractionThe aqueous phase was then extracted with EtOAc
  5. dry with materialthe organic extracts were dried (Na2SO4)
  6. customAfter evaporation of the solvent under reduced pressure
  7. customthe residue was purified by chromatography on silicagel (10% MeOH in CH2C2 with 1% Et3N)

Sources & evidence

ORD record
ord-20ef16efb14f4607b87bf53be64e2f5a
Source dataset
uspto-grants-2004_10
Patent number
US06800760B2

Reaction notes

Loading…