2-(2-Aminoethoxy)pyridine → N-[2-(2-Pyridyloxy)ethyl]3-Carbethoxymethyl-7,8-dimethoxypyrimido[4,5-b]quinolin-4(3H)-one-2-carboxamide

HRID 596598Notes

Reaction equation

HRID 596598 reaction equation
[C:1]([CH2:6][N:7]1[C:20](=[O:21])[C:19]2[C:10](=[N:11][C:12]3[C:17]([CH:18]=2)=[CH:16][C:15]([O:22][CH3:23])=[C:14]([O:24][CH3:25])[CH:13]=3)[N:9]=[C:8]1[C:26](OCC)=[O:27])([O:3][CH2:4][CH3:5])=[O:2].[N:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[O:37][CH2:38][CH2:39][NH2:40]>C(Cl)(Cl)Cl>[N:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[O:37][CH2:38][CH2:39][NH:40][C:26]([C:8]1[N:7]([CH2:6][C:1]([O:3][CH2:4][CH3:5])=[O:2])[C:20](=[O:21])[C:19]2[C:10]([N:9]=1)=[N:11][C:12]1[C:17]([CH:18]=2)=[CH:16][C:15]([O:22][CH3:23])=[C:14]([O:24][CH3:25])[CH:13]=1)=[O:27]

Participants

4

Reactant 2

HCID 968902-(2-Aminoethoxy)pyridineHCID 22752836ethyl 3-carbethoxymethyl-7,8-dimethoxypyrimido[4,5-b]quinolin-4(3H)-one-2-carboxylate

Product 1

HCID 21450316N-[2-(2-Pyridyloxy)ethyl]3-Carbethoxymethyl-7,8-dimethoxypyrimido[4,5-b]quinolin-4(3H)-one-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of ethyl 3-carbethoxymethyl-7,8-dimethoxypyrimido[4,5-b]quinolin-4(3H)-one-2-carboxylate (0.415 g., 1mM) and 2-(2-pyridyloxy)ethylamine (0.276 g., 2 mM) in chloroform (10 ml.) is refluxed for 24 hours. It is then cooled to room temperature and concentrated in vacuo. The residue, an oil, is crystallized by addition of ether until precipitation is complete. Yield = 0.41 g. (81%) of product; m.p. 170°-180° C.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue, an oil, is crystallized by addition of ether until precipitation

Sources & evidence

ORD record
ord-5118ef0be7d04fc99186124e4a15065f
Source dataset
uspto-grants-1977_03
Patent number
US04011324

Reaction notes

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