Methanol → HCID 67774099, compound

HRID 533423Notes

Reaction equation

HRID 533423 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[CH3:11].[CH3:12][C:13]1([CH3:21])[O:20][C:18](=[O:19])[CH2:17][C:15](=[O:16])[O:14]1.[CH:22]([O-])([O-])OC.CO>C(OCC)(=O)C>[CH3:12][C:13]1([CH3:21])[O:20][C:18](=[O:19])[C:17](=[CH:22][NH:1][C:2]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=2[CH3:11])[C:15](=[O:16])[O:14]1

Participants

6

Reactant 4

HCID 887MethanolHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 755984-Amino-3-methylbenzoic acidHCID 53629101Methylorthoformate

Product 1

HCID 67774099HCID 67774099, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-amino-3-methylbenzoic acid (7.3 g), Meldrum's acid (7.3 g), methyl orthoformate (5.6 g) and methanol (30 mL) was heated under stirring in an oil bath at 60° C. for 5 hours. The reaction mixture was returned to room temperature, diluted with ethyl acetate and the precipitate was collected by filtration to obtain 4-{[(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl]amino}-3-methylbenzoic acid (10.1 g).

Workup

  1. temperaturewas heated
  2. customwas returned to room temperature
  3. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-5d9c512a5c984526bb19d1f42ae4bc7a
Source dataset
uspto-grants-2014_10
Patent number
US08853242B2

Reaction notes

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