2-Methoxyaniline → HCID 178450493, compound

HRID 1382309Notes

Reaction equation

HRID 1382309 reaction equation
[CH3:1][O:2][C:3]1[C:4]([NH2:9])=[CH:5][CH:6]=[CH:7][CH:8]=1.[CH:10]([O:17]CC)([O:14][CH2:15][CH3:16])OCC.[C:20]([CH2:25][C:26](OCC)=O)(=[O:24])[CH2:21][CH2:22][CH3:23]>C(O)C>[C:20]([C:25](=[CH:26][NH:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1])[C:10]([O:14][CH2:15][CH3:16])=[O:17])(=[O:24])[CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 70002-MethoxyanilineHCID 31214Ethyl orthoformateHCID 238498Ethyl 3-oxohexanoate

Product 1

HCID 178450493HCID 178450493, compoundYield 27.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of o-anisidine (22.6 ml, 0.2 mol), triethyl orthoformate (33.3 ml, 0.2 mol) and ethyl butyrylacetate (31.6 ml, 0.2 mol) was heated such that ethanol distilled over slowly. After 2.5 hours the mixture was allowed to cool, diluted with methanol (100 ml) and allowed to crystallise. The N-(2-methoxyphenyl)-2-butyryl-3-(2-methoxyphenylamino)acrylamide by-product was filtered off. Evaporation of the mother liquors and recrystallisation from petroleum ether (40-60) gave ethyl 2-butyryl-3-(2-methoxyphenylamino)acrylate (15.82 g, 27.2%), m.p. 74°-76°.

Workup

  1. distillationdistilled over slowly
  2. temperatureto cool
  3. additiondiluted with methanol (100 ml)
  4. customto crystallise
  5. filtrationThe N-(2-methoxyphenyl)-2-butyryl-3-(2-methoxyphenylamino)acrylamide by-product was filtered off
  6. customEvaporation of the mother liquors and recrystallisation from petroleum ether (40-60)

Sources & evidence

ORD record
ord-dea392d7059746258a02ee999fe35fed
Source dataset
uspto-grants-1989_02
Patent number
US04806550

Reaction notes

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