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

HRID 1057373노트

반응식

HRID 1057373 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-ddfcd9e453f7476fbeeb3833e572df3e
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06514965B1

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