Hydrochloric Acid → HCID 22417662, compound

HRID 1720370Notes

Reaction equation

HRID 1720370 reaction equation
Cl.[CH3:2][OH:3].[CH2:4]([C:6]1[CH:7]=[CH:8][C:9]([C:13]#N)=[N:10][C:11]=1[CH3:12])[CH3:5].[OH2:15]>>[CH2:4]([C:6]1[CH:7]=[CH:8][C:9]([C:13]([O:3][CH3:2])=[O:15])=[N:10][C:11]=1[CH3:12])[CH3:5]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 962WaterHCID 22417671HCID 22417671, compound

Product 1

HCID 22417662HCID 22417662, compoundYield 87%

Procedure

Dry HCl (gas) was bubbled through a MeOH (30 mL) solution of 2-cyanopyridine from Step 1 (1.4 g, 9.6 mmol) at 0° C. until saturation. The flask was sealed with a new rubber septum and the reaction mixture was stirred 30 hours at r.t. After careful depressurisation, H2O (5 mL) was added and the MeOH was evaporated. The aqueous residue was neutralized with saturated aq. NaHCO3 and extracted with EtOAc (3×). The organic extracts were dried over MgSO4, concentrated in vacuo, and the residue was purified by flash chromatography (from 30% to 50% EtOAc in hexanes) to give 1.49 g (87%) of the title compound.

Workup

  1. customThe flask was sealed with a new rubber septum
  2. customthe MeOH was evaporated
  3. extractionextracted with EtOAc (3×)
  4. dry with materialThe organic extracts were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customthe residue was purified by flash chromatography (from 30% to 50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-0ee1ccd77e45469cbef5e72fb1b8a5e0
Source dataset
uspto-grants-1996_04
Patent number
US05506227

Reaction notes

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