Sodium Hydroxide → 1-Amino-1,4-dihydro-7-methyl-4-oxo-1,8naphthyridine-3-carboxylic acid

HRID 462693Notes

Reaction equation

HRID 462693 reaction equation
[NH2:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[N:10]=2)[C:5](=[O:13])[C:4]([C:14]([O:16]CC)=[O:15])=[CH:3]1.[OH-].[Na+]>O>[NH2:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[N:10]=2)[C:5](=[O:13])[C:4]([C:14]([OH:16])=[O:15])=[CH:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13457701Ethyl 1-amino-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate

Product 1

HCID 134577021-Amino-1,4-dihydro-7-methyl-4-oxo-1,8naphthyridine-3-carboxylic acidYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 10.0 g (0.0405 m) of ethyl 1-amino-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate, 1.94 g (0.0486 m) of sodium hydroxide and 350 ml of water was heated on a steam bath for two hours. The resulting solution was filtered, cooled and neutralized with 3 ml of acetic acid while stirring. The solid product was collected by filtration, washed with water and recrystallized by dissolving it in 100 ml of boiling dimethylformamide and adding 100 ml of ether to the cooled solution. There was obtained 7.8 g of 1-amino-1,4-dihydro-7-methyl-4-oxo-1,8naphthyridine-3-carboxylic acid, colorless needles, m.p. 239°-240° C.

Workup

  1. temperaturewas heated on a steam bath for two hours
  2. filtrationThe resulting solution was filtered
  3. temperaturecooled
  4. filtrationThe solid product was collected by filtration
  5. washwashed with water
  6. customrecrystallized
  7. dissolutionby dissolving it in 100 ml of boiling dimethylformamide
  8. additionadding 100 ml of ether to the cooled solution

Sources & evidence

ORD record
ord-f17a047c05be434e964e15839c0edb8a
Source dataset
uspto-grants-1985_05
Patent number
US04517191

Reaction notes

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