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

HRID 1778262Notes

Reaction equation

[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[Br:12].[CH3:13][C:14]1([CH3:22])[O:21][C:19](=[O:20])[CH2:18][C:16](=[O:17])[O:15]1.[CH:23](OCC)(OCC)OCC>C(O)(C)C>[Br:12][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:2]=1[NH:1][CH:23]=[C:18]1[C:19](=[O:20])[O:21][C:14]([CH3:22])([CH3:13])[O:15][C:16]1=[O:17])[C:6]([O:8][CH3:9])=[O:7]

Participants

Conditions

Temperature: 100 °C

Procedure

To a suspension of methyl 4-amino-3-bromobenzoate (2 g, 8.69 mmol) in isopropanol (10 mL) was added Meldrum's acid (1.63 g, 11 mmol) and triethyl orthoformate (5.26 mL, 31.6 mmol). The resulting mixture was heated at 100° C. for 4 hr and cooled to room temperature. The resulting precipitates were filtered off and washed with 10% Et2O/hexanes to yield methyl 3-bromo-4-(((2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl)amino)benzoate. (M+Na)+: 408.

Workup

temperaturecooled to room temperature
customThe resulting precipitates
filtrationwere filtered off
washwashed with 10% Et2O/hexanes

Sources & evidence

ORD record: ord-e9a960eb02714e29a5292f082a2f145e
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266835B2

Reaction notes

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