Sulfuric Acid → 1,3,4,5-Tetrahydro-2H-1-benzazepin-2-one

HRID 80526

반응식

HRID 80526 반응식
[C:1]1(=[O:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[N-:12]=[N+]=[N-].[Na+].S(=O)(=O)(O)O>C(Cl)(Cl)Cl>[NH:12]1[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3][CH2:2][C:1]1=[O:11]

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 107241-TetraloneHCID 33557Sodium Azide

생성물 1

HCID 2485801,3,4,5-Tetrahydro-2H-1-benzazepin-2-one

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

To an ice bath cooled solution of 3,4-dihydronaphthalen-1(2H)-one (20 mL, 150 mmol) in chloroform (300 mL) was added sodium azide (14.62 g, 225 mmol) and then concentrated sulfuric acid (80 mL, 1499 mmol) was added dropwise over 30 minutes, and the mixture was stirred at room temperature for 24 hours. The biphasic solution was poured into ice, and the product was extracted twice with ethyl acetate. The organic layer was washed with water, dried over Na2SO4 and concentrated to give the crude product which was purified by silica gel chromatography (Analogix IntelliFlash™ 280, SF 25-120) loading with dichloromethane and eluting with 30% ethyl acetate/hexanes to obtain the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 9.50 (s, 1H), 7.28-7.14 (m, 2H), 7.07 (td, J=7.4, 1.2, 1H), 7.00-6.85 (m, 1H), 2.67 (t, J=6.9, 2H), 2.20-2.03 (m, 4H); MS (ESI−) m/z 160.1 (M−H)−.

후처리

  1. additionThe biphasic solution was poured into ice
  2. extractionthe product was extracted twice with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give the crude product which
  7. customwas purified by silica gel chromatography (Analogix IntelliFlash™ 280, SF 25-120) loading with dichloromethane
  8. washeluting with 30% ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-e2952d18bf394046b718bb2500bf2346
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846663B2

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