Diethyl (ethoxymethylene)malonate → Diethyl{[(2-oxo-2H-1-benzopyran-3-yl)amino]methylene}malonate

HRID 2057467Notes

Reaction equation

HRID 2057467 reaction equation
[NH2:1][C:2]1[C:3](=[O:12])[O:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.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>>[CH2:21]([O:20][C:18](=[O:19])[C:17](=[CH:16][NH:1][C:2]1[C:3](=[O:12])[O:4][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=2[CH:11]=1)[C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH3:22]

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 742173-Aminocoumarin

Product 1

HCID 12377585Diethyl{[(2-oxo-2H-1-benzopyran-3-yl)amino]methylene}malonateYield 89.2%

Conditions

Temperature
120 °C

Procedure

A mixture of 3-aminocoumarin (30.0 g, 0.186 mole) and diethyl ethoxymethylenemalonate (75.0 g, 0.347 mole) is heated at 120° C. for 4 hours under nitrogen. The reaction mixture is cooled and triturated with hexane. The product is filtered off and washed with hexane. Recrystallization from ethyl acetate gives white crystals (55.0 g, 89%), mp. 134-135.

Workup

  1. temperatureThe reaction mixture is cooled
  2. customtriturated with hexane
  3. filtrationThe product is filtered off
  4. washwashed with hexane
  5. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-a87a2ceea0e0465499cbb0b8738a13d5
Source dataset
uspto-grants-1980_07
Patent number
US04210758

Reaction notes

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