3-Methoxyaniline → 5-[(3-Methoxyphenylamino)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 255166Notes

Reaction equation

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

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of m-anisidine (22 g, 178 mmol), 2,2-dimethyl-1,3-dioxane-4,6-dione (30.75 g, 214 mmol) and triethylorthoformate (30 mL, 178 mmol) in ethanol (200 mL) was heated at 85° C. for two hours. The mixture was allowed to cool to room temperature and the precipitate was collected by filtration and washed with ethanol to give 43.7 g (89% yield) of product as a pale yellow solid, mp 108° C.

Workup

temperatureto cool to room temperature
filtrationthe precipitate was collected by filtration
washwashed with ethanol

Sources & evidence

ORD record: ord-c9bead05849b4adca22307fc3629511f
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07875715B2

Reaction notes

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