Water → HCID 67010012, compound

HRID 2194542Notes

Reaction equation

HRID 2194542 reaction equation
[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([N:11]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][N:19]=4)[CH:14]=[C:13]([C:21]([O:23]CC)=[O:22])[C:12]3=[O:26])[CH:9]=[CH:10][C:2]1=2.O.[OH-].[Li+].O>O1CCOCC1>[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([N:11]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][N:19]=4)[CH:14]=[C:13]([C:21]([OH:23])=[O:22])[C:12]3=[O:26])[CH:9]=[CH:10][C:2]1=2

Participants

5

Reactant 3

HCID 962Water2×HCID 168937Lithium hydroxide, monohydrateHCID 67010559HCID 67010559, compound

Product 1

HCID 67010012HCID 67010012, compoundYield 101.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4.3 g (12 mmol) of ethyl 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate was dissolved in 1,4-dioxane (100 mL), and 1.0 g (24 mmol) of lithium hydroxide monohydrate and 50 mL of water were added thereto at room temperature. The resulting mixture was stirred overnight at room temperature. Water was added to the reaction mixture, and a solid precipitated therefrom was dissolved in chloroform. This solution was washed with an aqueous solution of citric acid and water in this order, and was dried and concentrated. The solid thus obtained was washed with diisopropyl ether, and thus 3.96 g of the title compound was obtained as pale yellow crystals (yield: quantitative).

Workup

  1. customat room temperature
  2. customa solid precipitated
  3. dissolutiontherefrom was dissolved in chloroform
  4. washThis solution was washed with an aqueous solution of citric acid and water in this order
  5. customwas dried
  6. concentrationconcentrated
  7. customThe solid thus obtained
  8. washwas washed with diisopropyl ether

Sources & evidence

ORD record
ord-44faa0ae1d2642838e4c464641fe5b1c
Source dataset
uspto-grants-2012_12
Patent number
US08334236B2

Reaction notes

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