Lithium hydroxide, monohydrate → HCID 76902673, compound

HRID 1497684Notes

Reaction equation

HRID 1497684 reaction equation
C([C:3]1[N:4]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:5]2[C:10]([C:11](=[O:16])[C:12]=1[C:13]([OH:15])=[O:14])=[N:9][CH:8]=[C:7]([Br:17])[CH:6]=2)C.O.[OH-].[Li+]>CO.O>[Br:17][C:7]1[CH:6]=[C:5]2[C:10]([C:11](=[O:16])[C:12]([C:13]([OH:15])=[O:14])=[CH:3][N:4]2[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[N:9][CH:8]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86725441HCID 86725441, compound

Product 1

HCID 76902673HCID 76902673, compoundYield 17.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a light brown solution of ethyl 7-bromo-4-oxo-1-(2-phenoxybenzyl)-1,4-dihydro-1,5-naphthyridine-3-carboxylate (22) (230 mg, 0.5 mmol) in methanol (20 mL) was added the solid lithium hydroxide monohydrate (438 mg, 10.4 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 brown paste was difficult to dissolve in 1.0N NaOH and water. Then, the neutral impurities were extracted into ethyl acetate and the basic aqueous layer was diluted with water (˜100 mL). Then, the 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, 40 mg of 7-bromo-4-oxo-1-(2-phenoxybenzyl)-1,4-dihydro-1,5-naphthyridine-3-carboxylic acid (23) (17% yield) was isolated as an off-white solid.

Workup

  1. customthe methanol was removed under vacuum
  2. dissolutionto dissolve in 1.0N NaOH
  3. extractionThen, the neutral impurities were extracted into ethyl acetate
  4. additionthe basic aqueous layer was diluted with water (˜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-17835a2f78404c6c861799b371483712
Source dataset
uspto-grants-2015_12
Patent number
US09199987B2

Reaction notes

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