Diphenyl Ether → HCID 178469578, compound

HRID 2290033Notes

Reaction equation

HRID 2290033 reaction equation
[C:1]([O:4][CH2:5][CH2:6][NH:7][C:8]1[CH:26]=[CH:25][C:11]([NH:12][CH:13]=[C:14]([C:20]([O:22]CC)=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:10][CH:9]=1)(=[O:3])[CH3:2].C1(OC2C=CC=CC=2)C=CC=CC=1>>[C:1]([O:4][CH2:5][CH2:6][NH:7][C:8]1[CH:9]=[C:10]2[C:11](=[CH:25][CH:26]=1)[N:12]=[CH:13][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:20]2[OH:22])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 7583Diphenyl EtherHCID 18698588HCID 18698588, compound

Product 1

HCID 178469578HCID 178469578, compoundYield 25.4%

Procedure

To a flask containing diethyl 2-[(4-{[2-(acetyloxy)ethyl]amino}anilino)-methylene]-malonate (0.18 g) is added diphenyl ether (2 mL). The reaction mixture is heated from room temperature to 250° C. over 30 minutes under a flow of argon gas. The reaction is cooled to room temperature and filtered. The collected precipitate is washed repeatedly with methanol:dichloromethane and the filtrate is concentrated under reduced pressure. The residue is adsorbed onto silica and chromatographed on silica eluting with 5% to 50% methanol in dichloromethane. The product-containing fractions are evaporated to give 0.04 g of ethyl 6-{[2-(acetyloxy)ethyl]amino}-4-hydroxy-3-quinolinecarboxylate.

Workup

  1. temperatureThe reaction mixture is heated from room temperature to 250° C. over 30 minutes under a flow of argon gas
  2. filtrationfiltered
  3. washThe collected precipitate is washed repeatedly with methanol
  4. concentrationdichloromethane and the filtrate is concentrated under reduced pressure
  5. customchromatographed on silica eluting with 5% to 50% methanol in dichloromethane
  6. customThe product-containing fractions are evaporated

Sources & evidence

ORD record
ord-ac6d9e80a46649dd9727c0d06922412c
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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