N-bromobutanimide → 1-Acetyl-8-bromo-7-hydroxy-2,3,4,5-tetrahydro-1H-benzazepine

HRID 1741045노트

반응식

HRID 1741045 반응식
[C:1]([N:4]1[C:10]2[CH:11]=[CH:12][C:13]([OH:15])=[CH:14][C:9]=2[CH2:8][CH2:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2].[Br:16]N1C(=O)CCC1=O>CC(O)=O.C(OCC)(=O)C>[C:1]([N:4]1[C:10]2[CH:11]=[C:12]([Br:16])[C:13]([OH:15])=[CH:14][C:9]=2[CH2:8][CH2:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2]

참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 218338251-Acetyl-7-hydroxy-2,3,4,5-tetrahydro-1H-benzazepine

생성물 1

HCID 218338021-Acetyl-8-bromo-7-hydroxy-2,3,4,5-tetrahydro-1H-benzazepine수율 31%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 8857Ethyl Acetate용매

실험 절차

1-Acetyl-7-hydroxy-2,3,4,5-tetrahydro-1H-benzazepine (D24, 2.81 g, 14 mmol) was stirred in glacial AcOH (50 ml) as N-bromosuccinimide (2.69 g, 15 mmol) was added portionwise over 20 min. The mixture was stirred for 30 min, diluted with ethyl acetate (500 ml), washed with water, K2CO3 solution and brine, dried (Na2SO4) and evaporated to give a tan solid, shown by NMR and TLC to be a mixture of dibromo and mono-bromo isomers. Chromatography on silica, eluting with 0-25% ethyl acetate/dichloromethane, yielded pure title compound (1.22 g, 31%) as a cream solid.

후처리

  1. additionwas added portionwise over 20 min
  2. washwashed with water, K2CO3 solution and brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customto give a tan solid
  6. additiona mixture of dibromo and mono-bromo isomers
  7. washChromatography on silica, eluting with 0-25% ethyl acetate/dichloromethane

출처 및 근거

ORD 기록
ord-7346bbfc15064b649313c71b761e3bb1
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05972951

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