2,2-Dimethyl-1,3-dioxane-4,6-dione → 5-((3-Hydroxy-4-methoxyanilino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 393594Notes

Reaction equation

HRID 393594 reaction equation
[CH3:1][C:2]1([CH3:10])[O:9][C:7](=[O:8])[CH2:6][C:4](=[O:5])[O:3]1.[OH:11][C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][C:18]=1[O:19][CH3:20])[NH2:15].[CH:21]([O-])([O-])OC>>[OH:11][C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][C:18]=1[O:19][CH3:20])[NH:15][CH:21]=[C:6]1[C:7](=[O:8])[O:9][C:2]([CH3:10])([CH3:1])[O:3][C:4]1=[O:5]

Participants

4

Reactant 3

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 743145-Amino-2-methoxyphenolHCID 53629101Methylorthoformate

Product 1

HCID 226465515-((3-Hydroxy-4-methoxyanilino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dioneYield 82%

Procedure

A solution of Meldrum's acid (32 g, 22.2 mmol)in methyl orthoformate (200 ml) was stirred at 100° C. 3-Hydroxy-4-methoxyaniline (28 g, 20 mmol) was added and the solution was heated at reflux for 15 minutes. After cooling, the mixture was stirred overnight at ambient temperature. The precipitate was collected by filtration, washed with methyl orthoformate followed by ether and dried under vacuum to give 5-((3-hydroxy-4-methoxyanilino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (47.5 g, 82%).

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for 15 minutes
  3. temperatureAfter cooling
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with methyl orthoformate
  6. customdried under vacuum

Sources & evidence

ORD record
ord-d2dd6c63b71c4d2492a86f0346c5eef9
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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