Boron tribromide → 8-Hydroxy-1,3,4,5-tetrahydrobenzo[b]azepin-2-one

HRID 1057373Notes

Reaction equation

HRID 1057373 reaction equation
C[O:2][C:3]1[CH:14]=[CH:13][C:6]2[CH2:7][CH2:8][CH2:9][C:10](=[O:12])[NH:11][C:5]=2[CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:14]=[CH:13][C:6]2[CH2:7][CH2:8][CH2:9][C:10](=[O:12])[NH:11][C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 6769538-methoxy-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one

Product 1

HCID 99205198-Hydroxy-1,3,4,5-tetrahydrobenzo[b]azepin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 8-methoxy-2,3,4,5-tetrahydro-1H-1-benzazepine-2-one (1.00 g, 5.23 mmol) in DCM (5 mL) was added dropwise 1M solution of BBr3 in DCM (5.23 mL). After stirring at room temperature for 30 min, the reaction mixture was heated at reflux for 5 hrs, allowed to cool to ambient temperature and poured into ice-water. The aqueous layer was extracted with DCM (5×10 mL), dried over Na2SO4, filtered and evaporated. The solid residue was washed with n-hexane and dried in high vacuum. The title compound was obtained as a white powder (705 mg, 76%). M.P.: 226-227° C.; MS (FAB): calcd for C10H11NO2 177.2; found m/e 178 (M+1)+.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 5 hrs
  3. temperatureto cool to ambient temperature
  4. extractionThe aqueous layer was extracted with DCM (5×10 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. washThe solid residue was washed with n-hexane
  9. customdried in high vacuum

Sources & evidence

ORD record
ord-ddfcd9e453f7476fbeeb3833e572df3e
Source dataset
uspto-grants-2003_02
Patent number
US06514965B1

Reaction notes

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