Methyl 2-(2-cyanophenoxy)acetate → 4,5-dihydro-1,4-benzoxazepin-3(2H)-one

HRID 540347Notes

Reaction equation

HRID 540347 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]1

Participants

4

Reactant 1

HCID 1472933Methyl 2-(2-cyanophenoxy)acetate

Product 1

HCID 9198014,5-dihydro-1,4-benzoxazepin-3(2H)-oneYield 67.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent2×

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

  1. customRaney Ni was removed by filtration
  2. concentrationthe filtrated was concentrated under reduced pressure
  3. customto give a residue which
  4. 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

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