Water → 2-Oxo-1-phenyl-1,2-dihydro-1,8-naphthyridine-3-carboxylic acid

HRID 2194528Notes

Reaction equation

[O:1]=[C:2]1[C:11]([C:12]([O:14]CC)=[O:13])=[CH:10][C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].O>O1CCOCC1>[O:1]=[C:2]1[C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 50 °C

Procedure

2.00 g (6.8 mmol) of ethyl 2-oxo-1-phenyl-1,2-dihydro-1,8-naphthyridine-3-carboxylate was dissolved in 1,4-dioxane (100 mL), and 1.41 g (10.2 mmol) of potassium carbonate and 200 mL of water were added thereto at room temperature. The resulting mixture was stirred for 3 hours at 50° C. The solvent was distilled off under reduced pressure from the reaction mixture, and the residue was dissolved in water. Concentrated hydrochloric acid was added thereto to make the solution acidic. A solid precipitated therefrom was separated by filtration, and was dried. Thus, 1.72 g of the title compound was obtained as pale yellow crystals (yield: 95%).

Workup

customat room temperature
distillationThe solvent was distilled off under reduced pressure from the reaction mixture
dissolutionthe residue was dissolved in water
additionConcentrated hydrochloric acid was added
customA solid precipitated
customtherefrom was separated by filtration
customwas dried

Sources & evidence

ORD record: ord-37d1196e022f42c68aace7823433f02f
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08334236B2

Reaction notes

Loading…