Methyl 2-(2-cyanophenoxy)acetate → 4,5-dihydro-1,4-benzoxazepin-3(2H)-one
Reaction equation
[C:1]([C:3]1[CH:14]=[CH:13][CH:12]=[CH:11][C:4]=1[O:5][CH2:6][C:7](OC)=[O:8])#[N:2]>CO.[Ni]>[O:5]1[C:4]2[CH:11]=[CH:12][CH:13]=[CH:14][C:3]=2[CH2:1][NH:2][C:7](=[O:8])[CH2:6]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
The methanol solution of methyl (2-cyanophenoxy)acetate (40 g, 0.209 mol) was added to the mixture of Raney Ni (80 g) in 500 mL of methanol. The reaction mixture was stirred at room temperature overnight under hydrogen atmosphere. Raney Ni was removed by filtration, and the filtrated was concentrated under reduced pressure to give a residue which was purified by column chromatography on silica gel (methanol/dichloromethane, 1:50) to give 23 g of product. MS obsd. (ESI+) [(M+H)+] 164.
Workup
- customRaney Ni was removed by filtration
- concentrationthe filtrated was concentrated under reduced pressure
- customto give a residue which
- customwas purified by column chromatography on silica gel (methanol/dichloromethane, 1:50)
Sources & evidence
- ORD record
- ord-50ee3a4e7691456db08c075c646dc4e7
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08871756B2
Reaction notes
Loading…