Diphenyl Ether → HCID 3245723, compound

HRID 525858Notes

Reaction equation

HRID 525858 reaction equation
C1(OC2C=CC=CC=2)C=CC=CC=1.C(O[C:17]([C:19]([C:33](=[O:35])[CH3:34])=[CH:20][NH:21][C:22]1[CH:32]=[CH:31][C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:24][CH:23]=1)=[O:18])C>CCCCCC>[C:33]([C:19]1[C:17](=[O:18])[C:23]2[C:22](=[CH:32][CH:31]=[C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:24]=2)[NH:21][CH:20]=1)(=[O:35])[CH3:34]

Participants

4

Reactant 2

HCID 7583Diphenyl EtherHCID 178471925HCID 178471925, compound

Product 1

HCID 3245723HCID 3245723, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
225 °C

Procedure

Diphenyl ether (150 ml, 943 mmol) was heated to boiling and ethyl 4-((2-(ethoxycarbonyl)-3-oxobut-1-en-1-yl)amino)benzoate (6.84 g, 22.40 mmol) was added slowly. After the addition, the reaction was allowed to stir at 200-250° C. for another 30 min. After cooling, the reaction was diluted with hexane, filtered, and the precipitate was washed with hexane/diethyl ether, collected and dried to give ethyl 3-acetyl-4-oxo-1,4-dihydroquinoline-6-carboxylate (5.74 g, 22.14 mmol, 99% yield) as tan solid. LCMS: (M+H)+: 260.0.

Workup

  1. additionwas added slowly
  2. additionAfter the addition
  3. temperatureAfter cooling
  4. filtrationfiltered
  5. washthe precipitate was washed with hexane/diethyl ether
  6. customcollected
  7. customdried

Sources & evidence

ORD record
ord-8be532b4d75746018f9a903ff41b2bec
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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