Sulfuric Acid → 5,7-Dimethyl-1,8-naphthyridin-2-ylamine

HRID 1395275Notes

Reaction equation

HRID 1395275 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH2:8])[N:3]=1.[CH3:9][C:10](=O)[CH2:11][C:12](=O)[CH3:13].S(=O)(=O)(O)O.[OH-].[Na+]>O.C(O)(=O)C>[NH2:8][C:4]1[N:3]=[C:2]2[C:7]([C:10]([CH3:9])=[CH:11][C:12]([CH3:13])=[N:1]2)=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 88612,6-DiaminopyridineHCID 14798Sodium HydroxideHCID 31261Acetylacetone

Product 1

HCID 973655,7-Dimethyl-1,8-naphthyridin-2-ylamine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

2,6-Diaminopyridine (43.6 g., 0.4 mole), 40.0 g (0.4 mole) of 2,4-pentanedione, 200 ml. of glacial acetic acid and 5 ml. of 96% sulfuric acid were mixed, then refluxed with stirring for 24 hours. The cold solution was added slowly with good stirring and ice bath cooling to 160 g of sodium hydroxide in enough water to make 600 ml. The brown solid, which crystallized, was filtered after the solution had been cooled overnight at 5°, washed twice with cold water and dried, 25.3 g., m.p. 125°-200°. This crude material was dissolved in 130 ml. of boiling 95% ethanol and the solution chilled overnight at -15°, 19.5 g. (28%), m.p. 215°-220°. This material was suitable for the following experiment.

Workup

  1. temperaturerefluxed
  2. additionThe cold solution was added slowly
  3. stirringwith good stirring
  4. customThe brown solid, which crystallized
  5. filtrationwas filtered after the solution
  6. temperaturehad been cooled overnight at 5°
  7. washwashed twice with cold water
  8. customdried
  9. dissolutionThis crude material was dissolved in 130 ml
  10. temperaturethe solution chilled overnight at -15°

Sources & evidence

ORD record
ord-8e9779388fb149afbec51e32c70bc169
Source dataset
uspto-grants-1980_05
Patent number
US04202981

Reaction notes

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