Hydrochloric Acid → 2'-Methyl-2-oxo-1,2-dihydro-3,4'-bipyridine-6-carboxylic acid, hydrochloride salt

HRID 2178683Notes

Reaction equation

HRID 2178683 reaction equation
C[O:2][C:3]1[C:8]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([CH3:15])[CH:10]=2)=[CH:7][CH:6]=[C:5]([C:16]([O:18]C)=[O:17])[N:4]=1.[ClH:20]>O1CCOCC1>[ClH:20].[CH3:15][C:11]1[CH:10]=[C:9]([C:8]2[C:3](=[O:2])[NH:4][C:5]([C:16]([OH:18])=[O:17])=[CH:6][CH:7]=2)[CH:14]=[CH:13][N:12]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68380339Methyl 2-methoxy-2'-methyl-3,4'-bipyridine-6-carboxylate

Product 1

HCID 1317313152'-Methyl-2-oxo-1,2-dihydro-3,4'-bipyridine-6-carboxylic acid, hydrochloride salt

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Methyl 2-methoxy-2′-methyl-3,4′-bipyridine-6-carboxylate (C32) (1.25 g, 4.84 mmol) was dissolved in dioxane (40 mL) and aqueous hydrochloric acid (37%, 40 mL), and heated to reflux for 18 hours. The reaction was cooled and concentrated to dryness, azeotroped with toluene and methanol and again concentrated to dryness. This process was repeated twice and the resulting solid was triturated three times with a 1:2:0.5 mixture of ethyl acetate/heptane/methanol to give the title compound as a yellow solid. Yield: 1.30 g, 4.87 mmol, quantitative. LCMS m/z 231.1 (M+1). 1H NMR (400 MHz, DMSO-d6) δ 2.76 (s, 3H), 7.08 (d, J=7.3 Hz, 1H), 8.24 (d, J=7.3 Hz, 1H), 8.31-8.38 (m, 2H), 8.76 (d, J=6.0 Hz, 1H), 12.2 (v br s, 1H).

Workup

  1. temperatureto reflux for 18 hours
  2. temperatureThe reaction was cooled
  3. concentrationconcentrated to dryness
  4. customazeotroped with toluene and methanol
  5. concentrationagain concentrated to dryness
  6. customthe resulting solid was triturated three times
  7. additionwith a 1:2:0.5 mixture of ethyl acetate/heptane/methanol

Sources & evidence

ORD record
ord-c80243cd6d0b42b689827e3b2451d53b
Source dataset
uspto-grants-2015_06
Patent number
US09067934B2

Reaction notes

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