2-Methoxyaniline → HCID 178496227, compound

HRID 1382327Notes

Reaction equation

HRID 1382327 reaction equation
[CH3:1][O:2][CH2:3][C:4](=[O:10])[CH2:5][C:6]([O:8][CH3:9])=[O:7].[C:11](OC(=O)C)(=O)C.C(OCC)(OCC)OCC.[CH3:28][O:29][C:30]1[C:31]([NH2:36])=[CH:32][CH:33]=[CH:34][CH:35]=1>>[CH3:1][O:2][CH2:3][C:4]([C:5](=[CH:11][NH:36][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[O:29][CH3:28])[C:6]([O:8][CH3:9])=[O:7])=[O:10]

Participants

5

Reactant 4

HCID 70002-MethoxyanilineHCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformateHCID 123500Methyl 4-methoxyacetoacetate

Product 1

HCID 178496227HCID 178496227, compoundYield 59.7%

Procedure

Methyl 4-methoxyacetoacetate (43 ml, 0.33 mol), acetic anhydride (31 ml, 0.33 mol) and triethyl orthoformate (110 ml, 0.66 mol) were heated under reflux for 2 hours, then the excess triethyl orthoformate and the produced ethyl acetate were evaporated from the mixture under reduced pressure. o-Anisidine (43 ml, 0.35 mol) was added and ethanol (15 ml) was distilled over under atmospheric pressure. When cool, the mixture was poured slowly into hexane to produce methyl 2-methoxyacetyl-3-(2-methoxyphenylamino)acrylate (55 g, 59.5%).

Workup

  1. temperatureunder reflux for 2 hours
  2. customthe excess triethyl orthoformate and the produced ethyl acetate were evaporated from the mixture under reduced pressure
  3. distillationethanol (15 ml) was distilled over under atmospheric pressure
  4. temperatureWhen cool
  5. additionthe mixture was poured slowly into hexane

Sources & evidence

ORD record
ord-0da0919f09ba4187a84ee42196aa641e
Source dataset
uspto-grants-1989_02
Patent number
US04806550

Reaction notes

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