Hydrochloric Acid → HCID 68380187, compound

HRID 2178648Notes

Reaction equation

HRID 2178648 reaction equation
C[O:2][C:3]1[N:8]=[C:7]([C:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[N:12]1[CH:16]=[C:15]([CH3:17])[N:14]=[CH:13]1.[ClH:18]>O1CCOCC1>[ClH:18].[CH3:17][C:15]1[N:14]=[CH:13][N:12]([C:4]2[C:3](=[O:2])[NH:8][C:7]([C:9]([OH:11])=[O:10])=[CH:6][CH:5]=2)[CH:16]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86671722HCID 86671722, compound

Product 1

HCID 68380187HCID 68380187, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridine-2-carboxylate (C2) (34.3 g, 139 mmol) in aqueous hydrochloric acid (37%, 230 mL) and 1,4-dioxane (230 mL) was heated at reflux for 18 hours. After cooling to room temperature, the reaction was filtered and the solids were washed with 1,4-dioxane (2×100 mL). The solids were mixed with methanol (500 mL) and the volatiles were removed in vacuo. The residue was stirred with methanol (100 mL) for 15 minutes, and 1,4-dioxane (250 mL) was added. The resulting mixture was stirred for 15 minutes; the solids were collected by filtration and washed with 1,4-dioxane to provide the title compound as a beige solid. Yield: 35.4 g, 138 mmol, 99%. 1H NMR (300 MHz, DMSO-d6) δ 2.33 (d, J=0.9 Hz, 3H), 7.09 (d, J=7.5 Hz, 1H), 7.84-7.87 (m, 1H), 8.04 (d, J=7.5 Hz, 1H), 9.50 (d, J=1.6 Hz, 1H).

Workup

  1. temperatureat reflux for 18 hours
  2. filtrationthe reaction was filtered
  3. washthe solids were washed with 1,4-dioxane (2×100 mL)
  4. additionThe solids were mixed with methanol (500 mL)
  5. customthe volatiles were removed in vacuo
  6. addition1,4-dioxane (250 mL) was added
  7. stirringThe resulting mixture was stirred for 15 minutes
  8. filtrationthe solids were collected by filtration
  9. washwashed with 1,4-dioxane

Sources & evidence

ORD record
ord-939dc28315a745979fb101fecc02372f
Source dataset
uspto-grants-2015_06
Patent number
US09067934B2

Reaction notes

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