Diphenyl Ether → Ethyl 6-bromo-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 1486925Notes

Reaction equation

HRID 1486925 reaction equation
C1(OC2C=CC=CC=2)C=CC=CC=1.[Br:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][CH:22]=[C:23]([C:29]([O:31]CC)=O)[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:17][CH:16]=1>CCOCC>[Br:14][C:15]1[CH:16]=[C:17]2[C:18](=[CH:19][CH:20]=1)[NH:21][CH:22]=[C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:29]2=[O:31]

Participants

4

Reactant 2

HCID 7583Diphenyl EtherHCID 1591151Diethyl 2-((4-bromophenylamino)methylene)malonate

Product 1

HCID 689824Ethyl 6-bromo-4-oxo-1,4-dihydroquinoline-3-carboxylateYield 92.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
240 °C

Procedure

Diphenyl ether (870 mL) was heated to 240° C. then diethyl 2-[[(4-bromophenyl)amino]methylidene]propanedioate (75 g, 219.18 mmol) added portionwise. The mixture was stirred at 240° C. for 60 minutes in a flask fitted with clean-stark apparatus. After cooling (25° C.) a crystallized solid was formed. The mixture was diluted with Et2O and the solid was collected by filtration, washed with Et2O and dried to afford the desired material (59.9 g) as a beige crystallized solid, which was used without purification or characterisation.

Workup

  1. customfitted with clean-stark apparatus
  2. temperatureAfter cooling (25° C.) a crystallized solid
  3. customwas formed
  4. filtrationthe solid was collected by filtration
  5. washwashed with Et2O
  6. customdried

Sources & evidence

ORD record
ord-cbf4eb7d456645b095e94111a482a6ef
Source dataset
uspto-grants-2016_08
Patent number
US09428503B2

Reaction notes

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