Diethyl (ethoxymethylene)malonate → Diethyl [(3-chloro-4-fluoroanilino)methylidene]propanedioate

HRID 1607993Notes

Reaction equation

HRID 1607993 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[F:9])[NH2:5].C(O[CH:13]=[C:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16])C>>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][CH:13]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:6]=[CH:7][C:8]=1[F:9]

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 97083-Chloro-4-fluoroaniline

Product 1

HCID 533801Diethyl [(3-chloro-4-fluoroanilino)methylidene]propanedioate

Procedure

3-Chloro-4-fluoroaniline (I) and diethyl ethoxymethylenemalonate were heated at 120°-130° C. to give diethyl (3-chloro-4-fluorophenyl)aminomethylenepropanedioate (II). The latter was cyclized by heating it at reflux in diphenyl ether to give the quinoline III.

Sources & evidence

ORD record
ord-b56274c66e3d428fa5071eb49519e154
Source dataset
uspto-grants-1989_09
Patent number
US04868305

Reaction notes

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