2-Methoxyaniline → HCID 178459173, compound

Reaction equation

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

Participants

Reactant 2

HCID 70002-Methoxyaniline

HCID 53662896Methyl 2-(methoxymethylidene)-3-oxopentanoate

Product 1

HCID 178459173HCID 178459173, compound

Procedure

A mixture of methyl 2-propanoyl-3-methoxyacrylate (70 g) and 2-methoxyaniline (45 ml) was heated on a steam bath for 30 minutes, then diluted with petroleum ether and left to crystallize. Filtration and washing with ether gave methyl 2-propanoyl-3-(2-methoxyphenylamino)acrylate (78.2 g) as a mixture of E/Z isomers.

Workup

temperaturewas heated on a steam bath for 30 minutes
waitleft
customto crystallize
filtrationFiltration
washwashing with ether

Sources & evidence

ORD record: ord-368e15fe99a64dd48d2a896fb240023f
Source dataset: uspto-grants-1992_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05089504

Reaction notes

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