Acetic Acid → HCID 86613911, compound

HRID 1811388Notes

Reaction equation

HRID 1811388 reaction equation
[Cl:1][C:2]([CH2:13][CH2:14][C:15]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]2[C:16]=1[CH:17]=[CH:18][C:19](=[O:28])[N:20]2[CH3:27])(C(OCC)=O)[C:3]([O:5]CC)=[O:4].C(O)(=O)C.Cl.O>C(O)C>[Cl:1][CH:2]([CH2:13][CH2:14][C:15]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]2[C:16]=1[CH:17]=[CH:18][C:19](=[O:28])[N:20]2[CH3:27])[C:3]([OH:5])=[O:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 962WaterHCID 66596981HCID 66596981, compound

Product 1

HCID 86613911HCID 86613911, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Diethyl 2-chloro-2-[2-(8-methoxy-1-methyl-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]malonate (2.38 g) was added to a mixture of acetic acid (10 ml) and 6N hydrochloric acid (15 ml), and the resulting mixture was heated under reflux overnight. After cooling to room temperature, water and a small quantity of ethanol was added to the reaction mixture, followed by ice cooling. The precipitated solid was collected by filtration, washed with water and dried to thereby obtain 0.99 g (yield: 55%) of 2-chloro-4-(8-methoxy-1-methyl-2-oxo-1,2-dihydroquinolin-5-yl)butyric acid as a gray powder.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux overnight
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-97836a9da8744c4caea330b979d58a69
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

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