Hydrochloric Acid → (1-Ethyl-7-hydroxy-2-oxo-1,2-dihydro-quinolin-3-yl)-acetic Acid Methyl Ester

HRID 2301975Notes

Reaction equation

HRID 2301975 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([OH:13])[CH:11]=2)[CH:6]=[C:5]([CH2:14][C:15]([OH:17])=[O:16])[C:4]1=[O:18])[CH3:2].Cl.[CH3:20]O>>[CH3:20][O:16][C:15](=[O:17])[CH2:14][C:5]1[C:4](=[O:18])[N:3]([CH2:1][CH3:2])[C:12]2[C:7]([CH:6]=1)=[CH:8][CH:9]=[C:10]([OH:13])[CH:11]=2

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 18462610(1-Ethyl-7-hydroxy-2-oxo-1,2-dihydro-quinolin-3-yl)-acetic Acid

Product 1

HCID 69978539(1-Ethyl-7-hydroxy-2-oxo-1,2-dihydro-quinolin-3-yl)-acetic Acid Methyl EsterYield 58%

Procedure

A suspension of (1-ethyl-7-hydroxy-2-oxo-1,2-dihydro-quinolin-3-yl)-acetic acid (2.9 g, 12 mmol) in methanol (30 mL) was treated with 12 N aqueous HCl (3 mL, 36 mmol) and the mixture heated to reflux. After 5 h, the resulting solution was cooled to room temperature, filtered and left standing overnight. The resulting solid was vacuum filtered, washed with ice-cold methanol and air-dried to give the title compound (1.8 g, 58% yield) as white needles.

Workup

  1. temperaturethe mixture heated to reflux
  2. filtrationfiltered
  3. waitleft
  4. waitstanding overnight
  5. filtrationfiltered
  6. washwashed with ice-cold methanol
  7. customair-dried

Sources & evidence

ORD record
ord-e28c01b734384cdbb2c5aad3ca73dc12
Source dataset
uspto-grants-2002_08
Patent number
US06429214B1

Reaction notes

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