Potassium Hydroxide → 1,4-Dihydro-7-methyl-1-methylamino-4-oxo-1,8-naphthyridine-3-carboxylic acid

HRID 462696Notes

Reaction equation

HRID 462696 reaction equation
[OH-].[K+].C([CH2:5][NH:6][N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH3:17])[N:15]=2)[C:10](=[O:18])[C:9]([C:19]([O:21]CC)=[O:20])=[CH:8]1)=O>O.C(O)C>[CH3:17][C:14]1[N:15]=[C:16]2[C:11]([C:10](=[O:18])[C:9]([C:19]([OH:21])=[O:20])=[CH:8][N:7]2[NH:6][CH3:5])=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 20397058ethyl 1-(N-formylmethylamino)-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate

Product 1

HCID 134577051,4-Dihydro-7-methyl-1-methylamino-4-oxo-1,8-naphthyridine-3-carboxylic acidYield 91%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 85% potassium hydroxide (2.25 g, 0.035 m) in 7.8 ml of water was added to a refluxing solution of 4.5 g (0.016 m) of ethyl 1-(N-formylmethylamino)-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate in 141 ml of absolute ethanol. The reaction mixture was heated at reflux for one hour, then allowed to stand at room temperature for three days, and poured into 100 ml of ice-water and filtered. The filtrate while cold was acidified with acetic acid, and the solid product was collected by filtration, washed with water and dried at 50° C. in vacuo to yield 3.3 g of 1,4-dihydro-7-methyl-1-methylamino-4-oxo-1,8-naphthyridine-3-carboxylic acid, beige solid, m.p. 215°-217° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for one hour
  3. filtrationfiltered
  4. filtrationthe solid product was collected by filtration
  5. washwashed with water
  6. customdried at 50° C. in vacuo

Sources & evidence

ORD record
ord-10063b606f764fbfae0a98532acf42e0
Source dataset
uspto-grants-1985_05
Patent number
US04517191

Reaction notes

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