N-methyl-2-pyrrolidone → HCID 68927458, compound

HRID 385541Notes

Reaction equation

HRID 385541 reaction equation
[CH3:1][N:2]1CCCC1=O.Br[C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15](=[O:25])[N:16]2[CH2:19][CH:20]2[O:24][CH2:23][CH2:22][O:21]2)=[N:11][CH:10]=1.[Cu](C#N)C#N>C(OCC)(=O)C>[C:1]([C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15](=[O:25])[N:16]2[CH2:19][CH:20]2[O:24][CH2:23][CH2:22][O:21]2)=[N:11][CH:10]=1)#[N:2]

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 578153037-bromo-1-(1,3-dioxolan-2-ylmethyl)-1,5-naphthyridin-2(1H)-oneHCID 178418260HCID 178418260, compound

Product 1

HCID 68927458HCID 68927458, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 10 mL of 1-methyl-2-pyrrolidinone, 358 mg of 7-bromo-1-(1,3-dioxolan-2-ylmethyl)-1,5-naphthyridin-2(1H)-one and 183 mg of copper cyanide were suspended, and the suspension was heated under reflux for 70 minutes. The reaction mixture was cooled to room temperature, ethyl acetate was then added thereto, the mixture was washed sequentially with water and a saturated saline water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography using silica gel; Silica Gel 60 made by KANTO CHEMICAL CO., INC., and an eluent of ethyl acetate:hexane 1:1 to obtain 145 mg of 7-cyano-1-(1,3-dioxolan-2-ylmethyl)-1,5-naphthyridin-2(1H)-one as a yellow solid.

Workup

  1. temperaturethe suspension was heated
  2. temperatureunder reflux for 70 minutes
  3. washthe mixture was washed sequentially with water
  4. dry with materiala saturated saline water and dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe resultant residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ff7c0460bec142409a1df6b387d31292
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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