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

HRID 1112238Notes

Reaction equation

HRID 1112238 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-af4f630cca354dc39d12e0570572ef56
Source dataset
uspto-grants-1978_10
Patent number
US04120962

Reaction notes

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