Hydrochloric Acid → 6-[(2-Methylindolizin-3-yl)carbonyl]-1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 535473Notes

Reaction equation

HRID 535473 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]2[N:11]([C:12]=1[C:13]([C:15]1[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=1)[N:21]([CH3:25])[CH:20]=[C:19]([C:26]([O:28]CC)=[O:27])[C:18]3=[O:31])=[O:14])[CH:10]=[CH:9][CH:8]=[CH:7]2.C(O)(C)(C)C.Cl>O>[CH3:3][C:4]1[CH:5]=[C:6]2[N:11]([C:12]=1[C:13]([C:15]1[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=1)[N:21]([CH3:25])[CH:20]=[C:19]([C:26]([OH:28])=[O:27])[C:18]3=[O:31])=[O:14])[CH:10]=[CH:9][CH:8]=[CH:7]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6386tert-ButanolHCID 14798Sodium HydroxideHCID 66652940Ethyl 6-[(2-methylindolizin-3-yl)carbonyl]-1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 666533896-[(2-Methylindolizin-3-yl)carbonyl]-1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acidYield 96.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.27 ml (3.22 mmol) of a 1N aqueous solution of sodium hydroxide is added, at ambient temperature, to 0.5 g (1.29 mmol) of ethyl 6-[(2-methylindolizin-3-yl)carbonyl]-1-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate in 9 ml of a mixture of t-butanol and water (1/1). The reaction medium is refluxed for 1 hour, acidified with a 1N aqueous solution of hydrochloric acid at ambient temperature, and then extracted with dichloromethane. The organic phase is washed with water, dried over sodium sulphate, and concentrated under reduced pressure. The residue obtained is rinsed with ether and then dried under reduced pressure at 50° C. 448 mg of a yellow solid are obtained.

Workup

  1. temperatureThe reaction medium is refluxed for 1 hour
  2. extractionextracted with dichloromethane
  3. washThe organic phase is washed with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue obtained
  7. washis rinsed with ether
  8. customdried under reduced pressure at 50° C

Sources & evidence

ORD record
ord-7a315499cb474984ac9005769d826a55
Source dataset
uspto-grants-2014_10
Patent number
US08859544B2

Reaction notes

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