Lithium hydroxide, monohydrate → HCID 86725442, compound

HRID 1497687Notes

Reaction equation

HRID 1497687 reaction equation
C([C:3]1[N:4]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[S:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)[C:5]2[C:10]([C:11](=[O:16])[C:12]=1[C:13]([OH:15])=[O:14])=[N:9][CH:8]=[CH:7][CH:6]=2)C.O.[OH-].[Li+]>CO.O>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([S:24][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[CH2:17][N:4]2[C:5]3[C:10](=[N:9][CH:8]=[CH:7][CH:6]=3)[C:11](=[O:16])[C:12]([C:13]([OH:15])=[O:14])=[CH:3]2)=[CH:26][CH:27]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86725443HCID 86725443, compound

Product 1

HCID 86725442HCID 86725442, compoundYield 53.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a light brown solution of ethyl 1-(2-(4-chlorophenylthio)benzyl)-4-oxo-1,4-dihydro-1,5-naphthyridine-3-carboxylate (26) (203 mg, 0.450 mmol) in methanol (20 mL) was added the solid lithium hydroxide monohydrate (189 mg, 4.5 mmol) at room temperature. The resulting light brown solution was stirred for 15 h at room temperature at which time LCMS analysis indicated the absence of starting material. Then, it was diluted with water and the methanol was removed under vacuum. The resulting light brown solids were difficult to dissolve in 1.0N NaOH and water, but it was dissolved in dimethylformamide (approx. 10 mL) and the solution was diluted with water (approx. 100 mL). Then, the resulting basic aqueous solution was neutralized with 1.0N HCl. The resulting solids were collected by filtration and washed with water and hexanes. After air drying, 102 mg of 1-(2-(4-chlorophenylthio)benzyl)-4-oxo-1,4-dihydro-1,5-naphthyridine-3-carboxylic acid (27) (53.6% yield) was isolated as an off-white solid.

Workup

  1. customthe methanol was removed under vacuum
  2. dissolutionto dissolve in 1.0N NaOH
  3. dissolutionwater, but it was dissolved in dimethylformamide (approx. 10 mL)
  4. additionthe solution was diluted with water (approx. 100 mL)
  5. filtrationThe resulting solids were collected by filtration
  6. washwashed with water and hexanes
  7. customAfter air drying

Sources & evidence

ORD record
ord-5edeb5a4743544799c5594297ee955d6
Source dataset
uspto-grants-2015_12
Patent number
US09199987B2

Reaction notes

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