O-Toluidine → HCID 178450484, compound

HRID 1382285Notes

Reaction equation

HRID 1382285 reaction equation
[C:1]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:5])[CH2:2][CH2:3][CH3:4].[CH:12](OCC)(OCC)OCC.C(OC(=O)C)(=O)C.[CH3:29][C:30]1[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=1[NH2:32]>>[C:1]([C:6](=[CH:12][NH:32][C:31]1[CH:33]=[CH:34][CH:35]=[CH:36][C:30]=1[CH3:29])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 4

HCID 7242O-ToluidineHCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformateHCID 238498Ethyl 3-oxohexanoate

Product 1

HCID 178450484HCID 178450484, compoundYield 38.6%

Procedure

A mixture of ethyl butyrylacetate (100 g, 0.63 mol), triethyl orthoformate (210 ml, 1.26 mol) and acetic anhydride (60 ml, 0.63 mol) was heated under reflux for 6 hours, then excess triethyl orthoformate evaporated in vacuo. 2-Methyl aniline (67 ml, 0.63 mol) was added to the residue, the mixture heated at reflux for 30 minutes then poured into petroleum ether. Filtration and washing gave ethyl 2-butyryl-3-(2-methylphenylamino)acrylate (67 g, 38%) as a mixture of E and Z isomers. The mother liquors were evaporated, taken up in ethyl acetate, washed with dilute hydrochloric acid, dried, evaporated and triturated with petroleum ether to give a further 57 g (33%) of ethyl 2-butyryl-3-(2-methylphenylamino)-acrylate.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hours
  3. customexcess triethyl orthoformate evaporated in vacuo
  4. temperaturethe mixture heated
  5. temperatureat reflux for 30 minutes
  6. filtrationFiltration
  7. washwashing

Sources & evidence

ORD record
ord-6d8f03e690e9469786e2439eae431125
Source dataset
uspto-grants-1989_02
Patent number
US04806549

Reaction notes

Loading…