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

HRID 1416937Notes

Reaction equation

HRID 1416937 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-a7061db6911f41bfad9bcce2cd97c594
Source dataset
uspto-grants-1999_06
Patent number
US05916898

Reaction notes

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