Isopropylamine → 1-Isopropyl-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid

HRID 524328Notes

Reaction equation

HRID 524328 reaction equation
CN([CH:4]=[C:5]1[C:10](=[O:11])[CH:9]=[C:8]([CH3:12])[O:7][C:6]1=[O:13])C.[CH:14]([NH2:17])([CH3:16])[CH3:15].CC(C)([O-])C.[Na+]>C(O)C>[CH:14]([N:17]1[C:8]([CH3:12])=[CH:9][C:10](=[O:11])[C:5]([C:6]([OH:13])=[O:7])=[CH:4]1)([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 14897943-(Dimethylaminomethylidene)-6-methylpyran-2,4-dioneHCID 23676156Sodium t-butoxide

Product 1

HCID 835312711-Isopropyl-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-dimethylaminomethylene-6-methyl-pyran-2,4-dione (preparation 3a, 10.00 g, 38.6 mmol based on 70% purity), isopropylamine (5.00 mL, 58.4 mmol) and sodium tert-butoxide (5.50 g, 57.2 mmol) in ethanol (20 mL) is heated for 18 h at 90° C. The reaction mixture is evaporated under reduced pressure, treated with water and extracted with dichloromethane. The aqueous layer is acidified with 4 N aqueous HCl and extracted with dichloromethane. The combined organic layer is washed with water, dried over Na2SO4 and evaporated under reduced pressure. Yield: 7.16 g; ESI mass spectrum: [M+H]+=196; Retention time HPLC: 0.71 min (Z002_006).

Workup

  1. customThe reaction mixture is evaporated under reduced pressure
  2. additiontreated with water
  3. extractionextracted with dichloromethane
  4. extractionextracted with dichloromethane
  5. washThe combined organic layer is washed with water
  6. dry with materialdried over Na2SO4
  7. customevaporated under reduced pressure
  8. custom0.71 min (Z002_006)

Sources & evidence

ORD record
ord-1a8f729a1c5846fba33d932e3efb9d49
Source dataset
uspto-grants-2016_05
Patent number
US09340507B2

Reaction notes

Loading…