HCID 68380187, compound → HCID 68379922, compound

HRID 2364957Notes

Reaction equation

HRID 2364957 reaction equation
[ClH:1].[CH3:2][C:3]1[N:4]=[CH:5][N:6]([C:8]2[C:13](=[O:14])[NH:12][C:11]([C:15]([OH:17])=O)=[CH:10][CH:9]=2)[CH:7]=1.CO[C:20]1[N:25]=[C:24]([C:26]([O-])=O)C=C[C:21]=1N1C=C(C)N=C1>Cl.O1CCOCC1>[Cl:1][CH2:21][CH2:20][N:25]1[CH2:24][CH2:26][N:12]2[C:13](=[O:14])[C:8]([N:6]3[CH:7]=[C:3]([CH3:2])[N:4]=[CH:5]3)=[CH:9][CH:10]=[C:11]2[C:15]1=[O:17]

Participants

5

Reactant 2

HCID 68380187HCID 68380187, compoundHCID 86671722HCID 86671722, compound

Product 1

HCID 68379922HCID 68379922, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

Synthesis of 5-(4-methyl-1H-imidazol-1-yl)-6-oxo-1,6-dihydropyridine-2-carboxylic acid, hydrochloride salt (C3). 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-7d4c97c07efb439bb484214837ca3e6d
Source dataset
uspto-grants-2014_04
Patent number
US08697673B2

Reaction notes

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