Hydrochloric Acid → HCID 178422969, compound

HRID 393936Notes

Reaction equation

HRID 393936 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:13]([O:15]CC)=[O:14].Cl>[OH-].[Na+]>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:13]([OH:15])=[O:14]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178469524Ethyl 7-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 178422969HCID 178422969, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Ethyl 4-hydroxy-7-methyl-3-quinolinecarboxylate (32 g, 138 mmol) was suspended in sodium hydroxide (500 mL of 10% aqueous) and then heated at reflux for about 30 minutes. The reaction mixture was allowed to cool to ambient temperature and then it was acidified with concentrated hydrochloric acid. The resulting precipitate was isolated by filtration, rinsed well with water and then oven dried to provide 4-hydroxy-7-methyl-3-quinolinecarboxylic acid (28 g). A portion (2 g) was recrystallized twice from N,N-dimethylformamide to give a fluffy white solid, m.p. 264-265° C. Analysis: Calculated for C11H9NO3: % C, 65.02; % H, 4.46; % N, 6.89; Found: % C, 65.22; % H, 4.42; % N, 6.88.

Workup

  1. temperatureheated
  2. temperatureat reflux for about 30 minutes
  3. customThe resulting precipitate was isolated by filtration
  4. washrinsed well with water
  5. customoven dried

Sources & evidence

ORD record
ord-6c20cc98341d4f8a951228b7c2387d2d
Source dataset
uspto-grants-2004_10
Patent number
US06809203B2

Reaction notes

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