Hydrogen Bromide → 9-Hydroxy-3,4-dihydro-1,4-benzoxazepin-5(2H)-one

HRID 1514219Notes

Reaction equation

HRID 1514219 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]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 162107589-methoxy-3,4-dihydro-1,4-benzoxazepin-5(2H)-one

Product 1

HCID 594035349-Hydroxy-3,4-dihydro-1,4-benzoxazepin-5(2H)-oneYield 76.7%

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

  1. customEvaporated to dryness
  2. customazeotroped with 200 ml of ethanol and biotage
  3. customchromatographed twice in 3% methanol in EtOAc
  4. customTriturated with EtOAc
  5. filtrationfiltered off

Sources & evidence

ORD record
ord-805640a041ab473790d01c79d2c1f27a
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

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