Ethyl Acetate → 7-Hydroxy-6-methyl-8-nitro-2H-oxazolo[3,2-A]pyridin-5(3H)-one
Reaction equation
[N+:1]([CH:4]=[C:5]1[NH:9][CH2:8][CH2:7][O:6]1)([O-:3])=[O:2].ClC1C=C(Cl)C=C(Cl)C=1[O:19][C:20](=O)[CH:21]([CH3:34])[C:22](OC1C(Cl)=CC(Cl)=CC=1Cl)=[O:23].C(OC(=O)C)C>C1(C)C(C)=CC=CC=1.CCCCCC>[OH:23][C:22]1[C:4]([N+:1]([O-:3])=[O:2])=[C:5]2[O:6][CH2:7][CH2:8][N:9]2[C:20](=[O:19])[C:21]=1[CH3:34]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 125 °C
Procedure
2-Nitromethylene-oxazolidine (3 g, 23.0 mmol) was added portion wise to a stirred solution of 2-methyl-malonic acid bis-(2,4,6-trichloro-phenyl) ester (12 g, 25.15 mmol) in Xylene (50 mL) under nitrogen atmosphere over a period of 1 hour at 125° C. The resulting mixture was heated to 125° C. for 5 hours. The reaction mixture was monitored by TLC (50% ethylacetate in hexane). The reaction mixture was concentrated and the concentrate was purified by column chromatography on silica gel (60% ethylacetate in hexane) to afford 1.5 g of the product (30% yield).
Workup
- concentrationThe reaction mixture was concentrated
- customthe concentrate was purified by column chromatography on silica gel (60% ethylacetate in hexane)
Sources & evidence
- ORD record
- ord-c79896ece7dd46848ac20a87e8627970
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08466289B2
Reaction notes
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