Dimethylformamide → 5,6-Dihydro-1-methyl-5-oxo-1,6-naphthyridin-1-ium monoiodide

HRID 274853Notes

Reaction equation

HRID 274853 reaction equation
[N:1]1[C:10]2[CH:9]=[CH:8][NH:7][C:6](=[O:11])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[I:12]C.[CH3:14]N(C)C=O>CC(C)=O>[I-:12].[CH3:14][N+:1]1[C:10]2[CH:9]=[CH:8][NH:7][C:6](=[O:11])[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 6328Methyl iodide2×HCID 55203681,6-naphthyridin-5(6H)-one

Product 1

HCID 200890325,6-Dihydro-1-methyl-5-oxo-1,6-naphthyridin-1-ium monoiodide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
25 °C

Procedure

A suspension of 5.85 g (40 mmol) of 1,6-naphthyridin-5(6H)-one (3), 10 mL of iodomethane, and 50 mL of anhydrous N,N-dimethylformamide is stirred at 25° C. for 19 hours. The suspension is treated with an additional 4 mL of iodomethane, stirred for 24 hours more, and poured slowly into 100 mL of stirring acetone. The solids are collected by filtration, washed with acetone, and dried to leave 10.54 g of pure product, mp 240°-244° C. The filtrate is concentrated in vacuo to give a solid residue that is triturated with 2-propanol and further processed to give 0.78 g of a second crop, mp 235°-240° C.

Workup

  1. stirringstirred for 24 hours more
  2. filtrationThe solids are collected by filtration
  3. washwashed with acetone
  4. customdried

Sources & evidence

ORD record
ord-b52eb6e3dfee4d3b8547bae2bb06ac19
Source dataset
uspto-grants-1995_02
Patent number
US05391554

Reaction notes

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