Sodium Hydroxide → 1,5-Dihydro-4,1-benzoxazepin-2(3H)-one

HRID 1891350Notes

Reaction equation

HRID 1891350 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][OH:13])=[O:4].[OH-].[Na+]>C(O)(C)C>[NH:5]1[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[CH2:12][O:13][CH2:2][C:3]1=[O:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 225912202-Chloro-N-[2-(hydroxymethyl)phenyl]acetamide

Product 1

HCID 158877541,5-Dihydro-4,1-benzoxazepin-2(3H)-oneYield 65%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To 2-chloro-N-(2-hydroxymethyl-phenyl)acetamide (7.0 g, 35 mmol) in isopropyl alcohol (100 mL) was added 50% w/w sodium hydroxide aqueous solution (4 mL, 50 mmol). The mixture was stirred at rt overnight. The mixture was extracted with DCM (50 mL×2). The resulting solution was then washed with brine (50 mL×2) and dried over MgSO4. The solvent was evaporated to afford 1,5-dihydro-4,1-benzoxazepin-2-one as a brown solid in 65% yield (3.7 g). MS: 163.0 (M+H)+; tR=1.56 min (method 1).

Workup

  1. extractionThe mixture was extracted with DCM (50 mL×2)
  2. washThe resulting solution was then washed with brine (50 mL×2)
  3. dry with materialdried over MgSO4
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-d3f618cc4a114a409324314190182f41
Source dataset
uspto-grants-2013_08
Patent number
US08507536B2

Reaction notes

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