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Structure of 16511-38-9

Chemical Structure| 16511-38-9

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Product Details of [ 16511-38-9 ]

CAS No. :16511-38-9
Formula : C10H9NO2
M.W : 175.18
SMILES Code : O=C(NC1=CC=CC=C12)CCC2=O
MDL No. :MFCD02167972
Boiling Point : No data available
InChI Key :VDTXDALRBZEUFV-UHFFFAOYSA-N
Pubchem ID :369398

Safety of [ 16511-38-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319
Precautionary Statements:P261-P302+P352-P305+P351+P338

Application In Synthesis of [ 16511-38-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 16511-38-9 ]
  • Downstream synthetic route of [ 16511-38-9 ]

[ 16511-38-9 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 16511-38-9 ]
  • [ 589-21-9 ]
  • [ 142273-20-9 ]
YieldReaction ConditionsOperation in experiment
58%
Stage #1: at 70℃; for 1 h;
Stage #2: With sulfuric acid In acetic acid at 70℃; for 1 h;
Bromophenylhydrazine (7 mmol) was added to a suspension of 2 (1.05 g, 6 mmol) in glacial acetic acid (10 ml) and then stirred for 1 h at 70° C. After cooling down it was stirred with 0.5 ml conc. H2SO4 for 1 h at 70° C. It was allowed to cool, poured into 50 ml of 10 percent sodium acetate solution and the precipitate was drawn off. Yellow crystals. Yield: 58percent. Mp.: >330° C. (1,4-dioxane). C16H11BrN2O (327.2). IR: 3220 (NH); 1640 cm-1 (CO). 1H NMR: δ (ppm): 11.75 (s; 1H, NH), 10.05 (s; 1H, NH), 7.89 (d; 1H, J=1.5 Hz, C-8-H), 7.74 (bd; 1H, J=7.5 Hz, Ar-H), 7.41-7.34 (m; 2H, Ar-H), 7.30-7.21 (m; 3H, Ar-H), 3.50 (s; 2H, CH2).
References: [1] Patent: WO2004/58766, 2004, A2, . Location in patent: Page/Page column 18.
[2] Patent: US2006/9445, 2006, A1, . Location in patent: Page/Page column 6.
[3] Archiv der Pharmazie, 1992, vol. 325, # 5, p. 297 - 299.
[4] European Journal of Medicinal Chemistry, 2010, vol. 45, # 1, p. 335 - 342.
  • 2
  • [ 16511-38-9 ]
  • [ 622-88-8 ]
  • [ 142273-20-9 ]
YieldReaction ConditionsOperation in experiment
79.6%
Stage #1: at 70℃; for 3 h;
Stage #2: at 70℃; for 3 h;
Stage #3: With sodium acetate In water
Example 3; 9-Bromo-7,12-dihydroindolo[3,2-d][1]-benzazepin-6(5H)-one (Compound 1.2); To a suspension of 1 H-[1]benzazepin-2,5(3H, 4H) -dione (0.247 g, 1.3 mmol) in acetic acid (5 ml) was added 4-bromophenylhydrazine hydrochloride (0.532 g, 2.3 mmol) and sodium acetate (0.195 g, 2.3 mmol) and stirred under argon. The mixture was heated at 70°C for 3 hours, then cooled and concentrated sulfuric acid (0.5 ml) added, before heating at 70°C for a further 3 hours. The slurry was poured into 10percent sodium acetate aqueous solution (20 ml) and the precipitate filtered to give the title compound as a cream solid (0.367 g, yield 79.6percent), mp > 300°C; 1 H- NMR (DMSO- d6,300 MHz) : No. (ppm) = 11.82 (s; 1 H), 10.1 (s; 1H), 7.89 (d; 1H), 7.74 (dd; 1H), 7.41-7.36 (m; 2H), 7.30-7.21 (m; 3H), 3.51 (s; 2H).
References: [1] Patent: WO2005/107471, 2005, A1, . Location in patent: Page/Page column 21.
 

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