Hydrochloric Acid → 6-Oxo-5-(2-propen-1-yl)-5,6-dihydro-1,5-naphthyridine-3-carboxylic Acid

HRID 656922Notes

Reaction equation

HRID 656922 reaction equation
[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]([C:12]([O:14]C)=[O:13])=[CH:5][C:4]=2[N:3]1[CH2:16][CH:17]=[CH2:18].[OH-].[Na+].Cl>O1CCOCC1.O>[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]([C:12]([OH:14])=[O:13])=[CH:5][C:4]=2[N:3]1[CH2:16][CH:17]=[CH2:18]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68816926Methyl 6-oxo-5-(2-propen-1-yl)-5,6-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 688095666-Oxo-5-(2-propen-1-yl)-5,6-dihydro-1,5-naphthyridine-3-carboxylic AcidYield 90.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of methyl 6-oxo-5-(2-propen-1-yl)-5,6-dihydro-1,5-naphthyridine-3-carboxylate (0.809 g, 3.32 mmol) in 1,4-dioxane (10 ml) and water (5 ml) was added 2M NaOH (2 ml) and the reaction was stirred at rt for 2 h. The pH of the mixture was then adjusted to 2-3 with 2M HCl and extracted three times with EtOAc. The combined organic phases were then dried and evaporated to give the desired product as a solid (0.689 g, 90%).

Workup

  1. extractionextracted three times with EtOAc
  2. customThe combined organic phases were then dried
  3. customevaporated

Sources & evidence

ORD record
ord-601694e576814e2898770699defead1e
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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