Hydrogen Bromide → 9-Hydroxy-3,4-dihydro-1,4-benzoxazepin-5(2H)-one
Reaction equation
C[O:2][C:3]1[C:13]2[O:12][CH2:11][CH2:10][NH:9][C:8](=[O:14])[C:7]=2[CH:6]=[CH:5][CH:4]=1.Br>>[OH:2][C:3]1[C:13]2[O:12][CH2:11][CH2:10][NH:9][C:8](=[O:14])[C:7]=2[CH:6]=[CH:5][CH:4]=1Participants
3
Conditions
- Temperature
- 105 °C
Procedure
9-(Methyloxy)-3,4-dihydro-1,4-benzoxazepin-5(2H)-one (Preparation 57) (9.3 g, 48.1 mmol) in hydrobromic acid (120 ml, 2210 mmol) was stirred and heated at 105° C. for 5 hours. Evaporated to dryness, azeotroped with 200 ml of ethanol and biotage chromatographed twice in 3% methanol in EtOAc. Triturated with EtOAc and filtered off to give 6.61 g of white solid. MS (ES): C9H9NO3 requires 179; found 180 [M+H]+.
Workup
- customEvaporated to dryness
- customazeotroped with 200 ml of ethanol and biotage
- customchromatographed twice in 3% methanol in EtOAc
- customTriturated with EtOAc
- filtrationfiltered off
Sources & evidence
- ORD record
- ord-805640a041ab473790d01c79d2c1f27a
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08222245B2
Reaction notes
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