Sodium ethoxide → HCID 67017331, compound

HRID 1842038Notes

Reaction equation

HRID 1842038 reaction equation
C([O:3][C:4](=O)[CH2:5][CH2:6][C:7]1[C:12]([NH2:13])=[CH:11][CH:10]=[C:9]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[N:8]=1)C.CC[O-].[Na+]>C(O)C>[F:21][C:20]([F:23])([F:22])[C:17]1[CH:18]=[CH:19][C:14]([C:9]2[N:8]=[C:7]3[C:12](=[CH:11][CH:10]=2)[NH:13][C:4](=[O:3])[CH2:5][CH2:6]3)=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 67017317HCID 67017317, compound

Product 1

HCID 67017331HCID 67017331, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.4 g 3-[3-Amino-6-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-propionic acid ethyl ester were dissolved in 200 ml ethanol. 2.41 g sodium ethylate were added and the reaction mixture stirred at room temperature for ten minutes and then at 60° C. for 1.5 hours. The cooled reaction mixture was evaporated in vacuo and the residue dissolved in 100 ml ethyl acetate and 200 ml 4M HCl were added. The mixture was vigorously stirred at room temperature. The organic lay was separated and washed with 100 ml 4M HCl. The combined aqueous layers were neutralized with NaOH. The precipitate was filtered, washed with water and dried under vacuo to obtain 1.87 g 6-(4-Trifluoromethyl-phenyl)-3,4-dihydro-1H-[1,5]naphthyridin-2-one.

Workup

  1. customThe cooled reaction mixture
  2. customwas evaporated in vacuo
  3. dissolutionthe residue dissolved in 100 ml ethyl acetate
  4. addition200 ml 4M HCl were added
  5. stirringThe mixture was vigorously stirred at room temperature
  6. customThe organic lay was separated
  7. washwashed with 100 ml 4M HCl
  8. filtrationThe precipitate was filtered
  9. washwashed with water
  10. customdried under vacuo

Sources & evidence

ORD record
ord-bda5e26c02c64e079fa3437d7f072ace
Source dataset
uspto-grants-2015_02
Patent number
US08946212B2

Reaction notes

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