Benzylamine → HCID 178526800, compound

HRID 639685Notes

Reaction equation

HRID 639685 reaction equation
Cl[C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[C:3]=1[N+:9]([O-:11])=[O:10].[CH2:12]([NH2:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:12]([NH:19][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([OH:8])[C:3]=1[N+:9]([O-:11])=[O:10])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 11430Potassium CarbonateHCID 5192824-Chloro-3-nitro-1,2-dihydropyridin-2-one

Product 1

HCID 178526800HCID 178526800, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

4-chloro-3-nitro-2-pyridone (5 g, 28.65 mmol) was suspended in 150 mL of acetonitrile then benzylamine (3.15 mL, 28.65 mmol) was added followed by potassium carbonate (4 g, 28.65 mmol) and the mixture was stirred at 60° C. overnight. The solvent was removed in vacuo and the residue was suspended in water (200 mL). A solution of HCl 2M was added until pH˜6. The precipitate was filtered and dried in vacuo to give 4.75g of the title compound as a beige solid. A second crop from the mother liquids provided 1.4 g of the title compound.

Workup

  1. customThe solvent was removed in vacuo
  2. additionA solution of HCl 2M was added until pH˜6
  3. filtrationThe precipitate was filtered
  4. customdried in vacuo

Sources & evidence

ORD record
ord-8208b30e7c9941e7836a2510317601ff
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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