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

HRID 80526

反応式

HRID 80526 の反応式
[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]

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 107241-TetraloneHCID 33557Sodium Azide

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

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)−.

後処理

  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

出典と根拠

ORDレコード
ord-e2952d18bf394046b718bb2500bf2346
出典データセット
uspto-grants-2014_09
特許番号
US08846663B2

関連ノート

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