Hydrochloric Acid → 1-(6-Bromo-pyridin-2-ylmethyl)-7-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid

HRID 226987Notes

Reaction equation

HRID 226987 reaction equation
[OH-].[Li+].C([O:5][C:6]([C:8]1[C:17](=[O:18])[C:16]2[C:11](=[N:12][C:13]([CH3:19])=[CH:14][CH:15]=2)[N:10]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([Br:27])[N:22]=2)[CH:9]=1)=[O:7])C.O.Cl>CO>[Br:27][C:23]1[N:22]=[C:21]([CH2:20][N:10]2[C:11]3[C:16](=[CH:15][CH:14]=[C:13]([CH3:19])[N:12]=3)[C:17](=[O:18])[C:8]([C:6]([OH:7])=[O:5])=[CH:9]2)[CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 577546221-(6-Bromo-pyridin-2-ylmethyl)-7-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester

Product 1

HCID 577547571-(6-Bromo-pyridin-2-ylmethyl)-7-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acidYield 69.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.110 g (4.62 mmol) of lithium hydroxide was added to 0.620 g of 1-(6-Bromo-pyridin-2-ylmethyl)-7-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester dissolved in 50 mL methanol and 100 mL of water and was heated at 60° C. for 3 hours. After the reaction was cooled to room temperature 1M HCl was added until the product precipitated from solution. The white solid was collected by vacuum filtration to yield 0.400 g of 1-(6-Bromo-pyridin-2-ylmethyl)-7-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid as a white solid.

Workup

  1. additionwas added until the product
  2. customprecipitated from solution
  3. filtrationThe white solid was collected by vacuum filtration

Sources & evidence

ORD record
ord-231a81ca76814064a39448084bb86f2e
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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