Hydrochloric Acid → 1-(6-Bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

HRID 227025Notes

Reaction equation

HRID 227025 reaction equation
C([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Br:24])[N:19]=2)[CH:7]=1)=[O:5])C.[OH-].[Li+].CO.Cl>CO.O>[Br:24][C:20]1[N:19]=[C:18]([CH2:17][N:8]2[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:15](=[O:16])[C:6]([C:4]([OH:5])=[O:3])=[CH:7]2)[CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 577546321-(6-Bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester

Product 1

HCID 577547691-(6-Bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acidYield 68.7%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
65 °C

Procedure

14.9 g (38.5 mmol) of 1-(6-bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester was dissolved/suspended in 300 mL of a 1:1 methanol-water mixture. 1.11 g (46.2 mmol) of lithium hydroxide was added and the mixture was heated up to 65° C. and stirred overnight. The mixture was cooled down to r.t., 300 mL of methanol and 4 mL of concentrated aqueous HCl were added and the solids were filtered off. The solids were then dissolved/suspended in 300 mL ethanol, brought to reflux, cooled down to rt, filtered, washed with 50 mL diethyl ether and dried to yield 9.5 g of the product as a white solid.

Workup

  1. temperatureThe mixture was cooled down to r.t.
  2. filtrationthe solids were filtered off
  3. temperatureto reflux
  4. temperaturecooled down to rt
  5. filtrationfiltered
  6. washwashed with 50 mL diethyl ether
  7. customdried

Sources & evidence

ORD record
ord-eac20ea6798b4b23a6aae33fc8a8d005
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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