4-Nitrophenol → 4-[[2-Methyl-4-oxo-3,4-dihydro-(2H)-1,3-benzoxazine-2-yl]methoxy]nitrobenzene
Reaction equation
[O:1]=[C:2]([CH3:14])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1.C([O-])([O-])=O.[K+].[K+].[N+]([C:24]1[CH:29]=[CH:28][C:27](O)=[CH:26][CH:25]=1)([O-])=O.ClCC(=O)C.C[N:37]([CH:39]=[O:40])C>>[CH3:14][C:2]1([CH2:3][O:4][C:5]2[CH:6]=[CH:7][C:8]([N+:11]([O-:13])=[O:12])=[CH:9][CH:10]=2)[NH:37][C:39](=[O:40])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[O:1]1Participants
6
Procedure
Preparation of 4-[2-oxo-propoxy]nitrobenzene—To stirred suspension of K2CO3 (50.0 g, 0.36 mol) in dry DMF (500 mL) was added 4-nitrophenol (25.0 g, 0.18 mol) and stirred for 30 min at 25° C. Chloroacetone (21.5 mL, 0.27 mol) was added to the reaction mixture and stirred for 24 h at 25-30° C. The reaction mixture was filtered through a buchner funnel. The filtrate was poured into water (500 mL) and extracted with ethyl acetate (3×300 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated. The crude compound was purified by column chromatography using EtOAc:Pet. ether (1:2) as eluent to yield the title compound (11.0 g, 31%) as a colourless liquid.
Workup
- stirringstirred for 30 min at 25° C
- stirringstirred for 24 h at 25-30° C
- filtrationThe reaction mixture was filtered through a buchner funnel
- additionThe filtrate was poured into water (500 mL)
- extractionextracted with ethyl acetate (3×300 mL)
- washThe combined organic layers were washed with brine
- dry with materialdried over anhydrous Na2SO4
- concentrationconcentrated
- customThe crude compound was purified by column chromatography
Sources & evidence
- ORD record
- ord-fdb711e1bc4648e9b8a2d38a9be45a7e
- Source dataset
- uspto-grants-2001_11
- Patent number
- US06313113B1
Reaction notes
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