Diethyl (ethoxymethylene)malonate → Diethyl {[(4-oxo-4H-1-benzopyran-3-yl)amino]methylene}propanedioate

HRID 1833365Notes

Reaction equation

HRID 1833365 reaction equation
[NH2:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[O:4][CH:3]=1.C(O[CH:16]=[C:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:18]([O:20][CH2:21][CH3:22])=[O:19])C>>[O:12]=[C:11]1[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[O:4][CH:3]=[C:2]1[NH:1][CH:16]=[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 122586463-Aminochromone

Product 1

HCID 12736915Diethyl {[(4-oxo-4H-1-benzopyran-3-yl)amino]methylene}propanedioateYield 62.5%

Conditions

Temperature
140 °C

Procedure

A mixture of 3-aminochromone (8.0 g, 0.05 mole) and diethyl ethoxymethylenemalonate (17.3 g, 0.08 mole) was heated under nitrogen at 140° C. for 2.5 hrs. The reaction mixture was cooled. The product, which crystallized out was filtered off and triturated with petroleum ether. Recrystallization from ethyl acetate - absolute ethanol gave white crystals (10.3 g, 62.5%), m.p. 155°-157° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customThe product, which crystallized out
  3. filtrationwas filtered off
  4. customtriturated with petroleum ether
  5. customRecrystallization from ethyl acetate - absolute ethanol

Sources & evidence

ORD record
ord-dfcc44e34ea84586a8a18ee988258ce6
Source dataset
uspto-grants-1978_01
Patent number
US04066655

Reaction notes

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