Hydrochloric Acid → Ethyl 4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate

HRID 67950Notes

Reaction equation

HRID 67950 reaction equation
[Na].[C:2]([O:10][CH2:11][CH3:12])(=[O:9])[CH2:3][C:4]([O:6]CC)=O.[CH3:13][N:14]1[C:19]2[N:20]=[CH:21][CH:22]=[CH:23][C:18]=2[C:17](=O)[O:16]C1=O.Cl>O.C(O)C>[OH:16][C:17]1[C:18]2[C:19](=[N:20][CH:21]=[CH:22][CH:23]=2)[N:14]([CH3:13])[C:4](=[O:6])[C:3]=1[C:2]([O:10][CH2:11][CH3:12])=[O:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 5360545SodiumHCID 125116271-Methyl-1H-pyrido[2,3-d][1,3]oxazine-2,4-dione

Product 1

HCID 54696179Ethyl 4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 0.345 g. (0.15 g. atom) of sodium in 30 ml. of ethanol was added 4.8 g. of diethyl malonate. The mixture was stirred at room temperature for 5 minutes and then was evaporated in a rotary evaporator. The residue was dissolved in 30 ml. of N,N-dimethylformamide and 2.67 g. (0.015 mole) of 1-methyl-1H-4H-pyrido[2,3-d][1,3]-oxazine-2,4-dione was added. The mixture was heated under reflux for 10 minutes and the thick mixture was dissolved in 100 ml. of water. The solution was acidified with conc. hydrochloric acid and the precipitate which formed was collected, air dried, and a small amount of this 1.7 g. was recrystallized from ethanol to give the analytical sample of 4-hydroxy-1,2-dihydro-1-methyl-2-oxo-1,8-naphthyridine-3-carboxylic acid, ethyl ester, m.p. 158°-160° C.

Workup

  1. customwas evaporated in a rotary evaporator
  2. dissolutionThe residue was dissolved in 30 ml
  3. temperatureThe mixture was heated
  4. temperatureunder reflux for 10 minutes
  5. dissolutionthe thick mixture was dissolved in 100 ml
  6. customthe precipitate which formed
  7. customwas collected
  8. customair dried
  9. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-3ecea573755444658f0ad32bf1ebe45a
Source dataset
uspto-grants-1982_08
Patent number
US04347362

Reaction notes

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