Diethyl Ether → HCID 13548560, compound

HRID 703443Notes

Reaction equation

HRID 703443 reaction equation
S(Cl)(Cl)=O.[O:5]=[C:6]1[CH:15]=[C:14]([CH2:16][C:17]([OH:19])=[O:18])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7]1.[CH3:20]COCC>CO>[O:5]=[C:6]1[CH:15]=[C:14]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24386Thionyl ChlorideHCID 47377352-(2-oxo-1,2-dihydroquinolin-4-yl)acetic acid

Product 1

HCID 13548560HCID 13548560, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

95 g (0.8 mol) of thionyl chloride are added dropwise in the course of approximately 1 h to a stirred suspension of 60 g (0.295 mol) of 2-oxo-1,2-dihydro-4-quinolineacetic acid in 1 1 of methanol. The mixture is left overnight. The solvent is driven off and the residue obtained is dissolved in 300 ml of boiling methanol. After the mixture is cooled, 300 ml of ether are added. The solid is drained and then recrystallized in methanol. 51.5 g (80%) of methyl 2-oxo-1,2-dihydro-4-quinolineacetate, melting point 209°-210° C., are obtained

Workup

  1. customthe residue obtained
  2. temperatureAfter the mixture is cooled
  3. customrecrystallized in methanol

Sources & evidence

ORD record
ord-06da27d9487f4fdfaa63a5c6f2454e5c
Source dataset
uspto-grants-1991_01
Patent number
US04983607

Reaction notes

Loading…