Lithium hydroxide, monohydrate → HCID 86720179, compound

HRID 1770666Notes

Reaction equation

HRID 1770666 reaction equation
[CH2:1]([S:3][C:4]1[C:13]([C:14]([O:16]CC)=[O:15])=[C:12]([CH3:19])[C:11]2[C:6](=[CH:7][N:8]=[CH:9][CH:10]=2)[N:5]=1)[CH3:2].O[Li].O>C1COCC1.CO.O>[CH2:1]([S:3][C:4]1[C:13]([C:14]([OH:16])=[O:15])=[C:12]([CH3:19])[C:11]2[C:6](=[CH:7][N:8]=[CH:9][CH:10]=2)[N:5]=1)[CH3:2]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86720180HCID 86720180, compound

Product 1

HCID 86720179HCID 86720179, compoundYield 41%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of ethyl 2-(ethylthio)-4-methyl-1,7-naphthyridine-3-carboxylate [synthesized according to the methods described for example 1, sections a-d] (2.30 g, 8.33 mmol, 1 eq) in a mixture of THF (30 ml) and methanol (15 ml) was added a solution of LiOH.H2O (3.50 g, 83.33 mmol, 10 eq) in water (7.5 ml) at RT. The resulting mixture was stirred at 75° C. for 5 h. Afterwards the solvents were evaporated and the residue was washed with EtOAc (80 ml). The aq. layer was acidified with a 4M aq. HCl (50 ml) and extracted with EtOAc (3×100 ml). The combined organic layers were washed with water (100 ml), brine (100 ml), dried over anhydrous Na2SO4 and evaporated to provide 2-(ethylthio)-4-methyl-1,7-naphthyridine-3-carboxylic acid (0.85 g, 3.43 mmol, 41%) which was used in subsequent reactions without further purification.

Workup

  1. customAfterwards the solvents were evaporated
  2. washthe residue was washed with EtOAc (80 ml)
  3. extractionextracted with EtOAc (3×100 ml)
  4. washThe combined organic layers were washed with water (100 ml), brine (100 ml)
  5. dry with materialdried over anhydrous Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-05e6bf3a46ec45e3b95549d00be756a2
Source dataset
uspto-grants-2016_02
Patent number
US09248122B2

Reaction notes

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