Diphenyl Ether → Ethyl 8-nitro-4-oxo-3,4-dihydroquinoline-3-carboxylate

HRID 1531684Notes

Reaction equation

HRID 1531684 reaction equation
[N+:1]([C:4]1[CH:22]=[CH:21][CH:20]=[CH:19][C:5]=1[NH:6][CH:7]=[C:8]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:9]([O:11]CC)=O)([O-:3])=[O:2].C1(OC2C=CC=CC=2)C=CC=CC=1>C(OCC)C>[CH2:17]([O:16][C:14]([CH:8]1[C:9](=[O:11])[C:19]2[C:5](=[C:4]([N+:1]([O-:3])=[O:2])[CH:22]=[CH:21][CH:20]=2)[N:6]=[CH:7]1)=[O:15])[CH3:18]

Participants

4

Reactant 2

HCID 7583Diphenyl EtherHCID 225911Diethyl 2-((2-nitrophenylamino)methylene)malonate

Product 1

HCID 21250014Ethyl 8-nitro-4-oxo-3,4-dihydroquinoline-3-carboxylateYield 85%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Diethyl (2-nitroanilino)methylenemalonate (43 g) was added to refluxing diphenyl ether (600 ml). The mixture was stirred at reflux for 1.5 hours, then cooled to ambient temperature. Diethyl ether (600 ml) was added and the mixture filtered. The solid so obtained was washed with diethyl ether to give 3-ethoxycarbonyl-8-nitro-4-oxo-3,4-dihydroquinoline in 85% yield, mp 241-243° C.

Workup

  1. temperatureat reflux for 1.5 hours
  2. filtrationthe mixture filtered
  3. customThe solid so obtained
  4. washwas washed with diethyl ether

Sources & evidence

ORD record
ord-167aae985859421983ba6f41f56afbe6
Source dataset
uspto-grants-2001_03
Patent number
US06200974B1

Reaction notes

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