Lithium hydroxide, monohydrate → HCID 76902485, compound

HRID 1497681Notes

Reaction equation

HRID 1497681 reaction equation
C([C:3]1[N:4]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]2[CH:30]=[CH:29][CH:28]=[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]=[C:7]([Br:17])[CH:6]=2)C.O.[OH-].[Li+]>CO.O>[C:20]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][N:4]1[C:5]2[C:10](=[N:9][CH:8]=[C:7]([Br:17])[CH:6]=2)[C:11](=[O:16])[C:12]([C:13]([OH:15])=[O:14])=[CH:3]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86725440HCID 86725440, compound

Product 1

HCID 76902485HCID 76902485, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a colorless solution of ethyl 1-(biphenyl-2-ylmethyl)-7-bromo-4-oxo-1,4-dihydro-1,5-naphthyridine-3-carboxylate (18) (50 mg, 0.11 mmol) in methanol (5 mL) was added solid lithium hydroxide monohydrate (22.6 mg, 0.54 mmol) at room temperature. The resulting colorless solution was stirred for 15 h at room temperature 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 resulting basic aqueous solution was diluted with water (˜50 mL) and 1.0N NaOH (˜10 mL) and then neutralized with 1.0N HCl. The resulting off-white solids were collected by filtration and washed with water and hexanes. After air drying, 32 mg of 1-(biphenyl-2-ylmethyl)-7-bromo-4-oxo-1,4-dihydro-1,5-naphthyridine-3-carboxylic acid (19) (67% yield) was isolated as an off-white solid.

Workup

  1. customthe methanol was removed under vacuum
  2. additionThe resulting basic aqueous solution was diluted with water (˜50 mL) and 1.0N NaOH (˜10 mL)
  3. filtrationThe resulting off-white solids were collected by filtration
  4. washwashed with water and hexanes
  5. customAfter air drying

Sources & evidence

ORD record
ord-de9b31a0acb44f1aa92ff6a5393931a2
Source dataset
uspto-grants-2015_12
Patent number
US09199987B2

Reaction notes

Loading…