Hydrochloric Acid → 8-Iodo-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 1864177Notes

Reaction equation

HRID 1864177 reaction equation
C([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[C:10]([I:17])[CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1)=[O:5])C.Cl>[OH-].[Na+].O>[I:17][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[NH:8][CH:7]=[C:6]([C:4]([OH:5])=[O:3])[C:15]2=[O:16]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 12403679Ethyl 4-hydroxy-8-iodoquinoline-3-carboxylate

Product 1

HCID 218975788-Iodo-4-oxo-1,4-dihydroquinoline-3-carboxylic acidYield 81.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

8-Iodo-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester (2 g, 5.83 mmol) was suspended in 10% NaOH in water (20 mL). The mixture was stirred under reflux for 1 h. The crude was cooled to room temperature and acidified with concentrated HCl. The solid was filtered off and thoroughly washed with water to afford 8-iodo-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid as a pinkish solid (1.5 g, 81.6%). 1H NMR (DMSO-d6, 400MHz) δ 7.04 (t, 1H), 8.12-8.16 (m, 2H), 8.71 (s, 1H). Exact mass calculated for C10H6INO3 314.94, found 316 (MH+).

Workup

  1. temperatureunder reflux for 1 h
  2. filtrationThe solid was filtered off
  3. washthoroughly washed with water

Sources & evidence

ORD record
ord-d7e3bc35311944d4a4c75a6e8365d495
Source dataset
uspto-grants-2009_12
Patent number
US07625906B2

Reaction notes

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