Ethyl 2-aminoquinoline-3-carboxylate → Ethyl 3,4-dihydro-4-oxopyrimido(4,5-b)quinoline-2-carboxylate

HRID 2163572Notes

Reaction equation

HRID 2163572 reaction equation
[C:1]([C:6](=[NH:8])[O-])([O:3][CH2:4][CH3:5])=[O:2].[NH2:9][C:10]1[C:19]([C:20](OCC)=[O:21])=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1>C(O)C>[N:9]1[C:10]2=[N:11][C:12]3[C:17]([CH:18]=[C:19]2[C:20](=[O:21])[NH:8][C:6]=1[C:1]([O:3][CH2:4][CH3:5])=[O:2])=[CH:16][CH:15]=[CH:14][CH:13]=3

Participants

4

Reactant 2

HCID 283477Ethyl 2-aminoquinoline-3-carboxylateHCID 227528221-Carbethoxyformimidate

Product 1

HCID 135765023Ethyl 3,4-dihydro-4-oxopyrimido(4,5-b)quinoline-2-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The same compound is obtained by: (a) refluxing equimolar amounts of 1-carbethoxyformimidate and ethyl 2-aminoquinoline-3-carboxylate in ethanol for three hours. The reaction mixture is concentrated, the product collected by filtration and recrystallized from hot chloroform; or (b) refluxing equimolar amounts of 1-carbethoxyformamidine and 2-aminoquinoline-3-carboxamide in ethanol for 3-4 hours in the presence of an equimolar amount of sodium ethoxide. The reaction mixture is worked up as described in (a) above.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. filtrationthe product collected by filtration
  3. customrecrystallized from hot chloroform
  4. temperatureor (b) refluxing equimolar amounts of 1-carbethoxyformamidine and 2-aminoquinoline-3-carboxamide in ethanol for 3-4 hours in the presence of an equimolar amount of sodium ethoxide

Sources & evidence

ORD record
ord-49f3c216da6448649d2fb3b8a8ac385a
Source dataset
uspto-grants-1979_01
Patent number
US04134981

Reaction notes

Loading…