Acetic Acid → HCID 178428446, compound

HRID 873931Notes

Reaction equation

HRID 873931 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH3:10])[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1.CC(O)=O>CCO>[Cl:11][C:12]1[CH:19]=[CH:18][C:15](/[CH:16]=[N:1]/[C:2]2[CH:3]=[C:4]([CH3:10])[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 77264-ChlorobenzaldehydeHCID 674566165-Amino-1,3-dimethyl-1,2-dihydropyridin-2-one

Product 1

HCID 178428446HCID 178428446, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

To a stirred solution of 5-amino-1,3-dimethylpyridin-2(1H)-one (Step 20.2) (5.2 g, 37.6 mmol) in EtOH (100 mL) were added 4-chlorobenzaldehyde (5.04 g, 35.8 mmol) and AcOH (0.410 mL, 7.17 mmol). The resulting mixture was heated up and stirred at 85° C. for 1 hr. The reaction was concentrated under reduced pressure and the resulting crude mixture was triturated in Et2O to afford the title product (7.6 g, 29.2 mmol) as beige solid. tR: 0.92 min (LC-MS 2).

Workup

  1. temperatureThe resulting mixture was heated up
  2. concentrationThe reaction was concentrated under reduced pressure
  3. customthe resulting crude mixture was triturated in Et2O

Sources & evidence

ORD record
ord-c96d60d406174b648dca590ba7a91976
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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