Diethyl (ethoxymethylene)malonate → Diethyl 6-ethoxy-3-pyridylaminomethylenemalonate

HRID 1956406Notes

Reaction equation

HRID 1956406 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:9][CH3:10])=[N:6][CH:7]=1.C(O[CH:14]=[C:15]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])C>>[CH2:9]([O:8][C:5]1[N:6]=[CH:7][C:2]([NH:1][CH:14]=[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:3][CH:4]=1)[CH3:10]

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 30403016-Ethoxypyridin-3-amine

Product 1

HCID 621746Diethyl 6-ethoxy-3-pyridylaminomethylenemalonate

Procedure

5-Amino-2-ethoxypyridine (9.25 g) and diethyl ethoxymethylenemalonate (14.5 g) was heated at 95° C. for 1 hour. On cooling in ice the oil solidified. The solid was ground up in petroleum ether (b.p. 60°-80° C.) and filtered to give diethyl 2-(6-ethoxy-3-pyridylaminomethylene)malonate, m.p. 68°-71° C.

Workup

  1. temperatureOn cooling in ice the oil
  2. filtrationfiltered

Sources & evidence

ORD record
ord-83571182e5f44bc29b9690f7a75f4de0
Source dataset
uspto-grants-1998_07
Patent number
US05780482

Reaction notes

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