Hydrochloric Acid → 7-Iodo-6-methyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

HRID 1374768Notes

Reaction equation

HRID 1374768 reaction equation
C([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][C:11]([I:18])=[C:12]([CH3:17])[CH:13]=2)[NH:8][CH:7]=1)=[O:5])C.Cl>[OH-].[Na+]>[I:18][C:11]1[CH:10]=[C:9]2[C:14]([C:15](=[O:16])[C:6]([C:4]([OH:5])=[O:3])=[CH:7][NH:8]2)=[CH:13][C:12]=1[CH3:17]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 694716687-Iodo-6-methyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester

Product 1

HCID 220544887-Iodo-6-methyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acidYield 99%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A suspension of 7-iodo-6-methyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester (8.30 g, 23.2 mmol) in 2 M aq. sodium hydroxide solution (80 mL) was heated at reflux for 2 h. After cooling the solution obtained was acidified with 25% aq. hydrochloric acid solution. The precipitate was collected by filtration and dried to afford the title compound (7.56 g, 99%). White solid, ISN-MS: m/e=327.9 ([M−H]−).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. temperatureAfter cooling the solution
  4. customobtained
  5. filtrationThe precipitate was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-5d4b6ff8009144f6947526a580f0ec16
Source dataset
uspto-grants-2007_01
Patent number
US07166589B2

Reaction notes

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