Sodium Hydroxide → 8-Fluoro-2-methoxy-4-quinolinecarboxylic acid

HRID 47432Notes

Reaction equation

HRID 47432 reaction equation
C[O:2][C:3]([C:5]1[C:14]2[C:9](=[C:10]([F:15])[CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]([O:16][CH3:17])[CH:6]=1)=[O:4].[OH-].[Na+]>CO>[F:15][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[N:8]=[C:7]([O:16][CH3:17])[CH:6]=[C:5]2[C:3]([OH:4])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 544876468-Fluoro-2-methoxyquinoline-4-carboxylic Acid Methyl Ester

Product 1

HCID 227451438-Fluoro-2-methoxy-4-quinolinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

8-Fluoro-2-methoxyquinoline-4-carboxylic acid methyl ester (0.1 82 g) in methanol (10 ml) containing 2N sodium hydroxide (0.41 ml) was stirred at room temperature for 16 h. Solvent was removed at reduced pressure, dissolved in water, and adjusted to pH2 with 2N hydrochloric acid. The precipitated title compound (0.155 g) was collected by filtration and dried. m/z (API−): 222 (MH+). 1H NMR δ: 4.02 (3H, s), 7.44-7.62 (3H, m), 8.31 (1H, d).

Workup

  1. customSolvent was removed at reduced pressure
  2. dissolutiondissolved in water
  3. customThe precipitated title compound (0.155 g)
  4. filtrationwas collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-99e2d3b1335843f0a3515c01d591ba7d
Source dataset
uspto-grants-2004_03
Patent number
US06699879B1

Reaction notes

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