Hydrochloric Acid → HCID 131719178, compound

HRID 863405Notes

Reaction equation

HRID 863405 reaction equation
C[O:2][C:3]([C:5]1([CH2:14][C:15]([O:17]C)=[O:16])[N:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]2=[N:7][CH2:6]1)=[O:4].[ClH:19]>>[ClH:19].[C:3]([C:5]1([CH2:14][C:15]([OH:17])=[O:16])[N:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]2=[N:7][CH2:6]1)([OH:4])=[O:2]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 19695894HCID 19695894, compound

Product 1

HCID 131719178HCID 131719178, compoundYield 51%

Procedure

The imidazopyridine ester product of Example 2 (0.057 g, 0.23 mmol) was dissolved in 4N HCl (4 mL) and heated to reflux for 14 h. All solvent was removed in vacuo and the residue triturated with diethyl ether to yield clean title compound (0.021 g, 51%). Anal. Calcd for C11H8 N2O4.1.1 HCl.0.9 H2O: C, 43.44; H, 3.97; N, 10.13; Cl, 14.10. Found: C, 43.32; H, 3.60; N, 10.18; Cl, 14.22. 1H NMR (300 MHz, DMSO): 4.5 (2H, s), 7.5 (1H, t, J=6.25 Hz), 7.95 (2H, m), 9 (1H, d, J=12.5 Hz).

Workup

  1. temperatureheated
  2. temperatureto reflux for 14 h
  3. customAll solvent was removed in vacuo
  4. customthe residue triturated with diethyl ether

Sources & evidence

ORD record
ord-e8bfab6d7665436da4978470f05f960d
Source dataset
uspto-grants-1998_02
Patent number
US05721223

Reaction notes

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