Hydrochloric Acid → HCID 178501821, compound

HRID 1374879Notes

Reaction equation

HRID 1374879 reaction equation
C([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)(=O)C.[C:10]([O:15][CH3:16])(=[O:14])[C:11]([O-:13])=O.[CH3:17][O-:18].[Na+].Cl.[CH3:21]O>>[CH3:16][O:15][C:10](=[O:14])[C:11]([OH:13])=[CH:21][C:17](=[O:18])[C:7]1[CH:6]=[N:5][CH:4]=[CH:9][CH:8]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 142862-AcetylpyridineHCID 10942334Sodium MethoxideHCID 21923985Methoxy(oxo)acetate

Product 1

HCID 178501821HCID 178501821, compound

Procedure

Acetyl pyridine (1.81 mL, 16.5 mmol) and methyl oxalate (3.12 g, 26.4 mmol) were dissolved in MeOH (30 mL, anhydrous). Sodium methoxide (6.9 mL, 25% in MeOH) was added over 10 min. Reaction solidified and was complete after 15 minutes. The solid mass was dissolved when acidified with HCl (10%, aqueous). The pH was then adjusted with NH4OH (conc) until precipitation ceased. The resulting solid was taken up in EtOAc. The aqueous layer was removed and extracted twice with EtOAc. The combined EtOAc layers were washed with water and brine, dried over MgSO4, filtered, and concentrated in vacuo. Collected 1 (2.90 g, 85%) as an off-white solid.

Workup

  1. customReaction
  2. dissolutionThe solid mass was dissolved when
  3. customThe pH was then adjusted with NH4OH (conc) until precipitation
  4. customThe aqueous layer was removed
  5. extractionextracted twice with EtOAc
  6. washThe combined EtOAc layers were washed with water and brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customCollected 1 (2.90 g, 85%) as an off-white solid

Sources & evidence

ORD record
ord-e4c93abd138f4f8b95c9b0cea7d5dc8e
Source dataset
uspto-grants-2007_01
Patent number
US07166619B2

Reaction notes

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