Diethyl (ethoxymethylene)malonate → HCID 21250004, compound

HRID 1531694Notes

Reaction equation

HRID 1531694 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([F:23])[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([C:12](=[O:22])[N:13]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:14])=[CH:7]2.C([O:26][CH:27]=[C:28]([C:34](OCC)=O)[C:29]([O:31][CH2:32][CH3:33])=[O:30])C>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH2:32]([O:31][C:29]([CH:28]1[C:27](=[O:26])[C:3]2[C:2](=[C:11]3[C:6](=[CH:5][C:4]=2[F:23])[CH:7]=[C:8]([C:12](=[O:22])[N:13]([CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH3:14])[CH:9]=[N:10]3)[N:1]=[CH:34]1)=[O:30])[CH3:33]

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 21250056HCID 21250056, compound

Product 1

HCID 21250004HCID 21250004, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

Using an analogous procedure to that described in Example 2, in the section relating to the preparation of starting materials, 8-amino-3-[N-benzyl-N-methylcarbamoyl]-6-fluoroquinoline was reacted with diethyl ethoxymethylenemalonate, and then refluxed in diphenyl ether. The product so obtained was recrystallised from a mixture of ethyl acetate and hexane to give 3-ethoxycarbonyl-8-(N-benzyl-N-methylcarbamoyl)-5-fluoro-4-oxo-3,4-dihydro-1,10-phenanthroline in 70% yield, mp 201-203° C.

Workup

  1. customThe product so obtained
  2. customwas recrystallised from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-823c4a057aca449589f4612b7ee501e7
Source dataset
uspto-grants-2001_03
Patent number
US06200974B1

Reaction notes

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