Hydrochloric Acid → HCID 59718745, compound

HRID 383530Notes

Reaction equation

HRID 383530 reaction equation
[OH-].[Na+].CO.C1COCC1.[CH2:10]([N:17]1[C:22]([CH2:23][CH3:24])=[C:21]([CH3:25])[CH:20]=[C:19]([C:26]([O:28]CC)=[O:27])[C:18]1=[O:31])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl>O>[CH2:10]([N:17]1[C:22]([CH2:23][CH3:24])=[C:21]([CH3:25])[CH:20]=[C:19]([C:26]([OH:28])=[O:27])[C:18]1=[O:31])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 59718769HCID 59718769, compound

Product 1

HCID 59718745HCID 59718745, compoundYield 83.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

2M sodium hydroxide solution (7.9 mL, 15.8 mmol) was added to a methanol/THF (7.9 mL/7.9 mL) solution of ethyl 1-benzyl-6-ethyl-5-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate (AA06, 1.92 g, 6.3 mmol), which had been obtained in Example 6, at room temperature and stirred at the same temperature for 2 hours. The reaction mixture was diluted with water (10 mL) and washed with ether (20 mL). 2M hydrochloric acid (8 mL, 16 mmol) was added to the water layer and the obtained mixture was extracted with ethyl acetate (20 mL) two times. The organic layer was washed with water (20 mL) two times and then dried with anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, and yellow oily 1-benzyl-6-ethyl-5-methyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid (AA07, 1.43 g) was obtained. The product was let alone for a night and was crystallized. The crystal was recrystallized from ethyl acetate and a white columnar crystal (AA07, 1.00 g, 58.5%) was obtained.

Workup

  1. customhad been obtained in Example 6, at room temperature
  2. washwashed with ether (20 mL)
  3. extractionthe obtained mixture was extracted with ethyl acetate (20 mL) two times
  4. washThe organic layer was washed with water (20 mL) two times
  5. dry with materialdried with anhydrous sodium sulfate
  6. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-33d96c9915e84d098a2070e85ba689b8
Source dataset
uspto-grants-2013_02
Patent number
US08367666B2

Reaction notes

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