Diethyl (ethoxymethylene)malonate → HCID 2267686, compound

HRID 542891Notes

Reaction equation

HRID 542891 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=1.C(O[CH:12]=[C:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])C>>[CH2:22]([O:21][C:19]([C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][NH:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=1)=[O:20])[CH3:23]

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 153472-Amino-3-methylpyridine

Product 1

HCID 2267686HCID 2267686, compoundYield 74.1%

Conditions

Temperature
135 °C

Procedure

A mixture of 2-amino-3-methylpyridine (5.5 g) and 2-ethoxy-1,1-bis(ethoxycarbonyl)ethene (10.8 g) was heated in a heating bath at 135° C. for 30 minutes. It was then cooled and triturated with light petroleum ether (b.p. 40°-60° C.). The resulting crude solid was recrystallised from light petroleum ether (b.p. 40°-60° C.), to give 1,1-bis(ethoxycarbonyl)-2-(3-methylpyrid-2-ylamino)ethene (10.3 g), m.p. 65°-67° C.

Workup

  1. temperatureIt was then cooled
  2. customtriturated with light petroleum ether (b.p. 40°-60° C.)
  3. customThe resulting crude solid was recrystallised from light petroleum ether (b.p. 40°-60° C.)

Sources & evidence

ORD record
ord-0de8d29102bd45bbb06484119cf11aac
Source dataset
uspto-grants-1987_04
Patent number
US04659727

Reaction notes

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