Hydrogen Bromide → 1-(2-Propen-1-yl)-1,8-naphthyridine-2,7(1H,8H)-dione
Reaction equation
[CH2:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14]CC=C)[N:12]=2)[CH:7]=[CH:6][C:5]1=[O:18])[CH:2]=[CH2:3].Br>C(O)(=O)C>[CH2:1]([N:4]1[C:13]2[NH:12][C:11](=[O:14])[CH:10]=[CH:9][C:8]=2[CH:7]=[CH:6][C:5]1=[O:18])[CH:2]=[CH2:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A solution of 1-(2-propen-1-yl)-7-(2-propen-1-yloxy)-1,8-naphthyridin-2(1H)-one (440 mg, 1.8 mmol) in acetic acid (1 ml) was treated with 33% hydrogen bromide in acetic acid (1 ml) and heated for 1 hour at 50° C. and 10 hours at 80° C. The mixture was evaporated to dryness and taken to pH4 with saturated aqueous sodium bicarbonate (˜5 ml). The mixture was extracted with ethyl acetate, dried and evaporated. The residue was chromatographed eluting with 0-100% ethyl acetate in hexane affording the product as a yellow oil (123 mg, 34%).
Workup
- customThe mixture was evaporated to dryness
- extractionThe mixture was extracted with ethyl acetate
- customdried
- customevaporated
- customThe residue was chromatographed
- washeluting with 0-100% ethyl acetate in hexane affording the product as a yellow oil (123 mg, 34%)
Sources & evidence
- ORD record
- ord-47174335b81540e699314484dcb80399
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08071592B2
Reaction notes
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