6-methoxy-3,4-dihydro-2H-1,4-benzoxazin-3-one → 6-Acetyl-2H-1,4-benzoxazin-3(4H)-one
Reaction equation
C([O:3][C:4](=O)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[CH:9][C:8]=1[N+:16]([O-])=O)C.COC1C=CC2OCC(=O)NC=2C=1>C(O)(=O)C.[Fe]>[C:13]([C:10]1[CH:11]=[CH:12][C:7]2[O:6][CH2:5][C:4](=[O:3])[NH:16][C:8]=2[CH:9]=1)(=[O:15])[CH3:14]Participants
5
Procedure
Ethyl(4-acetyl-2-nitrophenoxy)acetate (Intermediate 90) was reacted with iron in acetic acid as described for Intermediate 48. The crude product was obtained as an off white solid after work up. Recrystallization with ethyl acetate/methanol afforded the product as a colorless solid in 51% yield.
Workup
- customThe crude product was obtained as an off white solid after work up
- customRecrystallization with ethyl acetate/methanol
Sources & evidence
- ORD record
- ord-c056be5af8ee4101be58ebb686a0dde2
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08124602B2
Reaction notes
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