Diethyl (ethoxymethylene)malonate → HCID 12736916, compound

HRID 1833364Notes

Reaction equation

HRID 1833364 reaction equation
[NH2:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([Cl:13])[CH:9]=2)[O:4][CH:3]=1.C(O[CH:17]=[C:18]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:19]([O:21][CH2:22][CH3:23])=[O:20])C>>[Cl:13][C:8]1[CH:7]=[CH:6][C:5]2[O:4][CH:3]=[C:2]([NH:1][CH:17]=[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:11](=[O:12])[C:10]=2[CH:9]=1

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 123430803-Amino-6-chloro-4H-1-benzopyran-4-one

Product 1

HCID 12736916HCID 12736916, compoundYield 68.6%

Procedure

A mixture of 3-amino-6-chlorochromone (1.95 g, 0.01 mole) and diethyl ethoxymethylenemalonate (3.5 g, 0.016 mole) was heated under nitrogen at 120° for 4 hrs. The reaction mixture was cooled. The product, which precipitated, was filtered off and washed with ethyl acetate. Recrystallization from ethyl acetate gave white crystals (2.51 g, 68%), m.p. 143°-145°.

Workup

  1. temperaturewas heated under nitrogen at 120° for 4 hrs
  2. temperatureThe reaction mixture was cooled
  3. customThe product, which precipitated
  4. filtrationwas filtered off
  5. washwashed with ethyl acetate
  6. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-5e6009f11c544e6896d9fa20994f52d8
Source dataset
uspto-grants-1978_01
Patent number
US04066655

Reaction notes

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