Diphenyl Ether → HCID 178469570, compound

HRID 2290036Notes

Reaction equation

HRID 2290036 reaction equation
[O:1]=[C:2]1[N:6]([C:7]2[CH:25]=[CH:24][C:10]([NH:11][CH:12]=[C:13]([C:19]([O:21]CC)=O)[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:9][CH:8]=2)[CH2:5][CH2:4][O:3]1.C1(OC2C=CC=CC=2)C=CC=CC=1>C(OCC)C>[OH:21][C:19]1[C:24]2[C:10](=[CH:9][CH:8]=[C:7]([N:6]3[CH2:5][CH2:4][O:3][C:2]3=[O:1])[CH:25]=2)[N:11]=[CH:12][C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

4

Reactant 2

HCID 7583Diphenyl EtherHCID 18698544HCID 18698544, compound

Product 1

HCID 178469570HCID 178469570, compoundYield 42.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
235 °C

Procedure

To a flask containing diethyl 2-{[4-(2-oxo-1,3-oxazolidin-3-yl)anilino]-methylene}-malonate (0.46 g) is added diphenyl ether (6 mL). The reaction mixture is heated from room temperature to 235° C. over 2 hours under a flow of argon gas. After 1 hour at 235° C. the reaction is cooled to room temperature, diluted with diethyl ether and filtered. The collected precipitate is washed repeatedly with diethyl ether then dried in vacuo to give 0.17 g of ethyl 4-hydroxy-6-(2-oxo-1,3-oxazolidin-3-yl)-3-quinolinecarboxylate as a tan solid.

Workup

  1. temperatureThe reaction mixture is heated from room temperature to 235° C. over 2 hours under a flow of argon gas
  2. filtrationfiltered
  3. washThe collected precipitate is washed repeatedly with diethyl ether
  4. customthen dried in vacuo

Sources & evidence

ORD record
ord-792555dc76e74be5a9d2d62ce8594b11
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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