2,2-Dimethyl-1,3-dioxane-4,6-dione → Methyl 4-(((2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl)amino)-2-hydroxybenzoate

HRID 387913Notes

Reaction equation

[CH3:1][C:2]1([CH3:10])[O:9][C:7](=[O:8])[CH2:6][C:4](=[O:5])[O:3]1.[CH:11](OCC)(OCC)OCC.[NH2:21][C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[C:24]([OH:32])[CH:23]=1>CC(O)C>[CH3:1][C:2]1([CH3:10])[O:9][C:7](=[O:8])[C:6](=[CH:11][NH:21][C:22]2[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[C:24]([OH:32])[CH:23]=2)[C:4](=[O:5])[O:3]1

Participants

Conditions

Temperature: 100 °C

Procedure

After adding Meldrum acid (7.2 g, 50 mmol), triethyl orthoformate (50 ml) and 2-propanol (50 ml) to the publicly known compound methyl 4-amino-2-hydroxybenzoate (7.59 g, 45.4 mmol), the mixture was stirred at 100° C. for 1 hour. Upon cooling to room temperature, the precipitated crystals were filtered out, washed with diethyl ether and blow-dried to obtain the title compound (13.98 g, 43.5 mmol, 95.8%) as white crystals.

Workup

temperatureUpon cooling to room temperature
filtrationthe precipitated crystals were filtered out
washwashed with diethyl ether
customblow-dried

Sources & evidence

ORD record: ord-2a773fc96b5b4ace839134f9124fcd4e
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372981B2

Reaction notes

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