5-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione → 8-(2,2-Dimethyl-4,6-dioxo-1,3-dioxan-5-ylideneamino)-3-ethoxycarbonylquinoline

HRID 1531689Notes

Reaction equation

HRID 1531689 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][C:10]=2[NH2:16])=[O:5])[CH3:2].[CH3:17][C:18]1([CH3:29])[O:23][C:22](=[O:24])[C:21](=COC)[C:20](=[O:28])[O:19]1>C(O)C>[CH3:17][C:18]1([CH3:29])[O:23][C:22](=[O:24])[C:21](=[N:16][C:10]2[CH:11]=[CH:12][CH:13]=[C:14]3[C:9]=2[N:8]=[CH:7][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:15]3)[C:20](=[O:28])[O:19]1

Participants

4

Reactant 2

HCID 1521115-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dioneHCID 21250128Ethyl 8-aminoquinoline-3-carboxylate

Product 1

HCID 212500558-(2,2-Dimethyl-4,6-dioxo-1,3-dioxan-5-ylideneamino)-3-ethoxycarbonylquinolineYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-ethoxycarbonyl-8-amino-quinoline (9.9 g), 2,2-dimethyl-5-methoxymethylene-1,3-dioxan-4,6-dione (Monatsh. Chem., 98:564-78 (1967))(10.3 g) and ethanol (80 ml) was stirred at reflux for 2 hours. The mixture was cooled and filtered. The solid so obtained was washed with ethanol to give 8-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylideneamino)-3-ethoxycarbonylquinoline in 80% yield, mp 228-231° C.

Workup

  1. temperatureat reflux for 2 hours
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. customThe solid so obtained
  5. washwas washed with ethanol

Sources & evidence

ORD record
ord-bea1379caddf46f7b967a826e68de7eb
Source dataset
uspto-grants-2001_03
Patent number
US06200974B1

Reaction notes

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