Acetic Acid → HCID 86613910, compound

HRID 1811385Notes

Reaction equation

HRID 1811385 reaction equation
[Cl:1][C:2]([CH2:13][C:14]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]2[C:15]=1[CH:16]=[CH:17][C:18](=[O:27])[N:19]2[CH3:26])(C(OCC)=O)[C:3]([O:5]CC)=[O:4].C(O)(=O)C.Cl>O>[Cl:1][CH:2]([CH2:13][C:14]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]2[C:15]=1[CH:16]=[CH:17][C:18](=[O:27])[N:19]2[CH3:26])[C:3]([OH:5])=[O:4]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 66597041HCID 66597041, compound

Product 1

HCID 86613910HCID 86613910, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Diethyl 2-chloro-2-(8-methoxy-1-methyl-2-oxo-1,2-dihydroquinolin-5-ylmethyl)malonate (5.1 g) was added to a mixture of 20 ml of acetic acid and 15 ml of 6N hydrochloric acid, followed by heating under reflux for 9 hours. After cooling to room temperature, water was added to the reaction mixture, followed by cooling with ice. The precipitated solid was collected by filtration, washed with water and dried to thereby obtain 3.1 g of 2-chloro-3-(8-methoxy-1-methyl-2-oxo-1,2-dihydroquinolin-5-yl)propionic acid as a light yellow powder.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 9 hours
  3. temperatureby cooling with ice
  4. filtrationThe precipitated solid was collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-e6da0c57c2fc4dec938cdcb0c3443471
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

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