Acetic Acid → HCID 86613912, compound

HRID 1811391Notes

Reaction equation

HRID 1811391 reaction equation
[Cl:1][C:2]([CH2:13][CH2:14][CH2:15][C:16]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]2[C:17]=1[CH:18]=[CH:19][C:20](=[O:29])[N:21]2[CH3:28])(C(OCC)=O)[C:3]([O:5]CC)=[O:4].C(O)(=O)C.Cl>O>[Cl:1][CH:2]([CH2:13][CH2:14][CH2:15][C:16]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]2[C:17]=1[CH:18]=[CH:19][C:20](=[O:29])[N:21]2[CH3:28])[C:3]([OH:5])=[O:4]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 66596832HCID 66596832, compound

Product 1

HCID 86613912HCID 86613912, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Diethyl 2-chloro-2-[3-(8-methoxy-1-methyl-2-oxo-1,2-dihydroquinolin-5-yl)propyl]malonate (4.02 g) was added to a mixture of acetic acid (15 ml) and 6N hydrochloric acid (20 ml), followed by heating under reflux for 24 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 2.30 g (yield: 75%) of 2-chloro-5-(8-methoxy-1-methyl-2-oxo-1,2-dihydroquinolin-5-yl)valeric acid as a light yellow powder.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 24 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-6e3894ccf34940db9588b07ff65628e0
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

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