Hydrochloric Acid → HCID 68290699, compound

HRID 2174556Notes

Reaction equation

HRID 2174556 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:18])=[C:7](C(OCC)=O)[C:8](=[O:12])[NH:9]2)=[CH:4][C:3]=1[I:19].Cl>O1CCOCC1>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:18])=[CH:7][C:8](=[O:12])[NH:9]2)=[CH:4][C:3]=1[I:19]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68291064HCID 68291064, compound2×

Product 1

HCID 68290699HCID 68290699, compoundYield 42.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of ethyl 7-chloro-4-hydroxy-6-iodo-2-oxo-1,2-dihydro-3-quinolinecarboxylate (Intermediate 100) (2 g, 5.08 mmol) in 1,4-dioxane (10 mL) was added concentrated hydrochloric acid (3 mL, 36.5 mmol) and the reaction mixture was stirred 72 h at 80° C. After cooling, the reaction mixture was evaporated and the resulting solid was filtered, washed with water and dried to give the title compound 7-chloro-4-hydroxy-6-iodo-2(1H)-quinolinone (700 mg, 2.177 mmol, 42.8% yield) as cream solid. LCMS: (M+H)+=322; Rt=2.26 min.

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was evaporated
  3. filtrationthe resulting solid was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-2db3ee75efe54ae59e8ff1a4355e54f7
Source dataset
uspto-grants-2015_06
Patent number
US09061998B2

Reaction notes

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