3-Aminobenzamide → {1-[3-(aminocarbonyl)phenyl]-4-hydroxy-6-oxo-1,6-dihydropyridin-2-yl}methyl Acetate

HRID 1867165

Reaction equation

HRID 1867165 reaction equation
[C:1]([O:4][CH2:5][C:6](=O)[CH2:7][C:8]1[O:13]C(C)(C)O[C:10](=[O:16])[CH:9]=1)(=[O:3])[CH3:2].[NH2:18][C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[C:22]([NH2:24])=[O:23].CS(O)(=O)=O>O1CCOCC1>[C:1]([O:4][CH2:5][C:6]1[N:18]([C:19]2[CH:27]=[CH:26][CH:25]=[C:21]([C:22]([NH2:24])=[O:23])[CH:20]=2)[C:10](=[O:16])[CH:9]=[C:8]([OH:13])[CH:7]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 16453-AminobenzamideHCID 6395Methanesulfonic AcidHCID 220507863-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)-2-oxopropyl acetate

Product 1

HCID 54724225{1-[3-(aminocarbonyl)phenyl]-4-hydroxy-6-oxo-1,6-dihydropyridin-2-yl}methyl Acetate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

3-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)-2 oxopropyl acetate (4.00 g, 16.52 mmol) was dissolved in 1,4-dioxane (160 mL) and 3-aminobenzamide (1.73 g, 12.71 mmol) was added. The reaction was heated to reflux for 1 hour then cooled to 70° C. Methanesulfonic acid (1.22 g, 12.71 mmol) was added and the reaction brought back to reflux for 1 hour. The reaction was cooled to room temperature, concentrated and used as crude product for the next step.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 1 hour
  3. temperatureto reflux for 1 hour
  4. temperatureThe reaction was cooled to room temperature
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5271992453c94787ac69eacdc858e2b7
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Linked notes

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