Dimethyl acetylenedicarboxylate → HCID 86735049, compound

HRID 2071244Notes

Reaction equation

HRID 2071244 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:14]([C:20]([O:22][CH3:23])=[O:21])#[C:15][C:16]([O:18][CH3:19])=[O:17]>CO>[Cl:13][C:8]1[CH:7]=[CH:6][C:5]2[O:4][CH:3]=[C:2]([NH:1][C:15](=[CH:14][C:20]([O:22][CH3:23])=[O:21])[C:16]([O:18][CH3:19])=[O:17])[C:11](=[O:12])[C:10]=2[CH:9]=1

Participants

4

Reactant 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 123430803-Amino-6-chloro-4H-1-benzopyran-4-one

Product 1

HCID 86735049HCID 86735049, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-amino-6-chlorochromone (8 g, 0.041 mole) and dimethyl acetylenedicarboxylate (10.5 g, 0.074 mole) in methanol (150 ml) was stirred at room temperature for 2 days. The product was filtered off and washed with methanol. Recrystallization from ethyl acetate gave yellow crystals (11 g, 80%), m.p. 158°-160°.

Workup

  1. filtrationThe product was filtered off
  2. washwashed with methanol
  3. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-fd6038b7847d4d47bbe5df8b28986452
Source dataset
uspto-grants-1977_09
Patent number
US04046769

Reaction notes

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