Lithium hydroxide, monohydrate → HCID 76072889, compound

HRID 1497688Notes

Reaction equation

HRID 1497688 reaction equation
C([C:3]1[N:4]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=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:30][C:27]1[CH:28]=[CH:29][C: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:25][CH:26]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86725444HCID 86725444, compound

Product 1

HCID 76072889HCID 76072889, compoundYield 69.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a brown solution of ethyl 1-((4′-chlorobiphenyl-2-yl)methyl)-4-oxo-1,4-dihydro-1,5-naphthyridine-3-carboxylate (28) (257 mg, 0.61 mmol) in methanol (15 mL) was added the solid lithium hydroxide monohydrate (515 mg, 12.3 mmol) at room temperature under a nitrogen atmosphere. It gave a clear solution within 30 minutes and the resulting dark brown solution was stirred for 15 h at which time LCMS analysis indicated the absence of starting material. Then, the mixture was diluted with water and the methanol was removed under vacuum. The basic aqueous layer was diluted with water and the brown solids were filtered off using filter paper. Then, the filtrate was neutralized with 1.0N HCl. The precipitated off-white solids were collected by filtration and washed with water and hexanes. After drying in air, 165 mg of 1-((4′-chlorobiphenyl-2-yl)methyl)-4-oxo-1,4-dihydro-1,5-naphthyridine-3-carboxylic acid (29) (68.8% yield) was isolated as an off-white solid.

Workup

  1. customIt gave a clear solution within 30 minutes
  2. customthe methanol was removed under vacuum
  3. additionThe basic aqueous layer was diluted with water
  4. filtrationthe brown solids were filtered off
  5. filtrationusing filter paper
  6. filtrationThe precipitated off-white solids were collected by filtration
  7. washwashed with water and hexanes
  8. customAfter drying in air

Sources & evidence

ORD record
ord-4f07c239a0704dd392cefcffaf40fe1a
Source dataset
uspto-grants-2015_12
Patent number
US09199987B2

Reaction notes

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