Hydrochloric Acid → 1-(2-aminoethyl)-5,7-dimethyl-1,8-naphthyridine-2(1H)-one hydrochloride

HRID 2163335Notes

Reaction equation

HRID 2163335 reaction equation
C1(=O)[N:5]([CH2:6][CH2:7][N:8]2[C:17]3[C:12](=[C:13]([CH3:19])[CH:14]=[C:15]([CH3:18])[N:16]=3)[CH:11]=[CH:10][C:9]2=[O:20])C(=O)C2=CC=CC=C12.NN.[ClH:29].C(NN)(=O)C1C(=CC=CC=1)C(NN)=O>C(O)C.O>[ClH:29].[NH2:5][CH2:6][CH2:7][N:8]1[C:17]2[C:12](=[C:13]([CH3:19])[CH:14]=[C:15]([CH3:18])[N:16]=2)[CH:11]=[CH:10][C:9]1=[O:20]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 9321HydrazineHCID 11367556PhthalohydrazideHCID 233354051-(2-phthalimidoethyl)-5,7-dimethyl-1,8-naphthyridin-2(1H)-one

Product 1

HCID 233353711-(2-aminoethyl)-5,7-dimethyl-1,8-naphthyridine-2(1H)-one hydrochloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 1-(2-phthalimidoethyl)-5,7-dimethyl-1,8-naphthyridin-2(1H)-one (5.2 gm., 0.015 mole) and 95% hydrazine (1.8 ml., 0.053 mole) in absolute ethanol (50 ml.) is refluxed for one hour. The reaction is cooled, water (37.8 ml.) and concentrated hydrochloric acid (37.5 ml.) are added. After refluxing for one half hour, the mixture is cooled in an ice bath and phthalhydrazide (2.85 gm., 0.0125 mole) is filtered off. The filtrate is concentrated and the residue is dissolved in water, made basic with saturated sodium carbonate and extracted with methylene chloride. The organic layer is dried over anhydrous sodium sulfate, filtered and evaporated. The residue containing the free base of the title compound is dissolved in a minimum amount of methanol and treated with ethereal hydrogen chloride. Recrystallization of the product from isopropanol gives 1-(2-aminoethyl)-5,7-dimethyl-1,8-naphthyridine-2(1H)-one hydrochloride melting at 253.5-254.5° C.

Workup

  1. temperatureis refluxed for one hour
  2. temperatureThe reaction is cooled
  3. temperatureAfter refluxing for one half hour
  4. temperaturethe mixture is cooled in an ice bath
  5. concentrationThe filtrate is concentrated
  6. dissolutionthe residue is dissolved in water
  7. extractionextracted with methylene chloride
  8. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. additionThe residue containing the free base of the title compound
  12. dissolutionis dissolved in a minimum amount of methanol
  13. additiontreated with ethereal hydrogen chloride
  14. customRecrystallization of the product from isopropanol

Sources & evidence

ORD record
ord-f0418d57ae1d459eb55e93e48d2e289f
Source dataset
uspto-grants-1979_01
Patent number
US04133885

Reaction notes

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