Sodium hydride → 7-Methyl-1, 6-naphthyridine-5 (6H)-one

HRID 274852Notes

Reaction equation

HRID 274852 reaction equation
[CH3:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[H-].[Na+].CN(C)[C:15](=O)[CH3:16]>>[CH3:15][C:16]1[NH:6][C:4](=[O:5])[C:3]2[CH:7]=[CH:8][CH:9]=[N:10][C:2]=2[CH:1]=1

Participants

4

Reactant 3

HCID 24758Sodium hydride2×HCID 31374Dimethylacetamide2×HCID 122437052-Methylnicotinamide

Product 1

HCID 218622147-Methyl-1, 6-naphthyridine-5 (6H)-one

Conditions

Temperature
50 °C

Procedure

A mixture of 272.3 mg (2 mmol) of 2-methylnicotinamide (2) and 0.34 mL (2.2 mmol) of 95% N,N-dimethylacetamide, dimethylacetal is heated at 50° C. for 1.5 hours, then a vacuum is applied for 1 hour with heating as described above. The oil is diluted with 2 mL of dry N,N-dimethylacetamide, treated with 96 mg of 60% sodium hydride, and heated at 80° C. for 2.5 hours. The solution is treated with 70 mg more of 60% sodium hydride, heated for an addition 4.5 hours, then quenched with excess acetic acid. The mixture is concentrated at 2 mm/70° C. to leave a residual solid that is triturated in hot chloroform, then filtered through a pad of silica gel (230-400 mesh). The pad is eluted with chloroform, then acetone to collect the product. The filtrate is concentrated to a solid that is dissolved in a minimum volume of hot water. The solution is stored at 5° C. for 2 weeks, and the precipitated solids are collected by filtration, washed well with propanol, and dried to give 73 mg of pure product, mp 244°-245° C.

Workup

  1. temperaturewith heating
  2. temperatureheated at 80° C. for 2.5 hours
  3. temperatureheated for an addition 4.5 hours
  4. customquenched with excess acetic acid
  5. concentrationThe mixture is concentrated at 2 mm/70° C.
  6. customto leave a residual solid
  7. customthat is triturated in hot chloroform
  8. filtrationfiltered through a pad of silica gel (230-400 mesh)
  9. washThe pad is eluted with chloroform
  10. customacetone to collect the product
  11. concentrationThe filtrate is concentrated to a solid
  12. dissolutionthat is dissolved in a minimum volume of hot water
  13. waitThe solution is stored at 5° C. for 2 weeks
  14. filtrationthe precipitated solids are collected by filtration
  15. washwashed well with propanol
  16. customdried

Sources & evidence

ORD record
ord-db479a2681b941dd8e8ef5977bf02f7e
Source dataset
uspto-grants-1995_02
Patent number
US05391554

Reaction notes

Loading…