Diethyl (ethoxymethylene)malonate → Diethyl (6-ethoxy-2-pyridylamino)methylenemalonate

HRID 128609Notes

Reaction equation

HRID 128609 reaction equation
[CH2:1]([O:3][C:4]1[N:9]=[C:8]([NH2:10])[CH:7]=[CH:6][CH:5]=1)[CH3:2].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>>[CH2:1]([O:3][C:4]1[N:9]=[C:8]([NH:10][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:7]=[CH:6][CH:5]=1)[CH3:2]

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 5867106-Ethoxy-2-pyridinamine

Product 1

HCID 86749097Diethyl (6-ethoxy-2-pyridylamino)methylenemalonate

Conditions

Temperature
95 °C

Procedure

A mixture of 6-ethoxypyridin-2-amine (8.0 g) and diethyl ethoxymethylenemalonate (12.5 g) was heated at 95° C. under vacuum for 3 hours and then heated at 95° C. at atmospheric pressure for 18 hours. The mixture was cooled to ambient temperature, diluted with petroleum ether b.p. 40°-60° C. and filtered to give diethyl (6-ethoxy-2-pyridylamino)methylenemalonate, m.p. 58°-60° C.

Workup

  1. temperatureheated at 95° C. at atmospheric pressure for 18 hours
  2. temperatureThe mixture was cooled to ambient temperature
  3. filtrationfiltered

Sources & evidence

ORD record
ord-6ba1fa986b1a415ca28e0a6d84dcfd3e
Source dataset
uspto-grants-1995_11
Patent number
US05464781

Reaction notes

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