Hydrochloric Acid → HCID 67354449, compound

HRID 1093049Notes

Reaction equation

HRID 1093049 reaction equation
[N:1]1[CH:6]=[C:5]([C:7]([OH:9])=[O:8])[CH:4]=C(C(O)=O)[CH:2]=1.C[O:14][C:15]([O:18][CH3:19])([CH3:17])C.[ClH:20].[CH3:21]O>>[ClH:20].[CH3:21][O:9][C:7]([C:5]1[CH:6]=[N:1][CH:2]=[C:17]([C:15]([O:18][CH3:19])=[O:14])[CH:4]=1)=[O:8]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 64952,2-DimethoxypropaneHCID 103663,5-Pyridinedicarboxylic acid

Product 1

HCID 67354449HCID 67354449, compoundYield 86%

Conditions

Temperature
23 °C

Procedure

To pyridine-3,5-dicarboxylic acid (19.9 g, 119.1 mmol) in methanol (400 mL) was added of 2,2-dimethoxypropane (160 mL, 1.3 mol) and concentrated HCl (15 mL). The reaction mixture was refluxed for 18 h under an atmosphere of Ar. The solvent was evaporated then ether (100 mL) was added to the crude material and the resulting mixture heated to reflux. The mixture was allowed to remain at reflux for 2 hours then s allowed to cool to 23° C. and the precipitate filtered. The precipitate was dried to afford 27.5 g (86% yield) of the title compound as described in J. Org. Chem. Vol. 16, No 10, 1996. LCMS (+ESI, M+H+) m/z: 196.

Workup

  1. temperatureThe reaction mixture was refluxed for 18 h under an atmosphere of Ar
  2. customThe solvent was evaporated
  3. additionether (100 mL) was added to the crude material
  4. temperaturethe resulting mixture heated to reflux
  5. temperatureat reflux for 2 hours
  6. filtrationthe precipitate filtered
  7. customThe precipitate was dried

Sources & evidence

ORD record
ord-2016c2dcfcba45f89c720b327fd32bc0
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

Loading…