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Chemical Structure| 87700-67-2 Chemical Structure| 87700-67-2

Structure of 87700-67-2

Chemical Structure| 87700-67-2

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Product Details of [ 87700-67-2 ]

CAS No. :87700-67-2
Formula : C12H9ClO
M.W : 204.65
SMILES Code : O=C(Cl)C1=C2C=CC=CC2=C(C)C=C1
MDL No. :MFCD12025362

Safety of [ 87700-67-2 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P301+P330+P331-P303+P361+P353-P363-P304+P340-P310-P321-P260-P264-P280-P305+P351+P338-P405-P501
Class:8
UN#:3261
Packing Group:

Application In Synthesis of [ 87700-67-2 ]

* 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.

  • Downstream synthetic route of [ 87700-67-2 ]

[ 87700-67-2 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 4488-40-8 ]
  • [ 87700-67-2 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; for 0.25h;Heating / reflux; To a stirred solution of 0.080 g (0.50 mmol) of 1-propylindole in 1.5 mL of dry CH2Cl2 at 0 C. under N2 was added dropwise 0.75 mL (0.75 mmol) of Me2AlCl (1 M in hexanes). The solution was stirred at 0 C. for 30 min and a solution of 0.122 g (0.6 mmol) of freshly prepared 4-methyl-1-naphthoyl chloride in 1.5 mL of CH2Cl2. The acid chloride was prepared form 0.122 g (0.60 mmol) of 4-methyl-1-naphthoic acid to which was added dropwise 1 mL of thionyl chloride at a rate sufficient to maintain a steady evolution of gas. This solution was heated at reflux for 15 min, cooled to ambient temperature and the excess thionyl chloride was removed in vacuo to give the acid chloride which was used without further purification. The deep red acylation reaction mixture was stirred at 0 C. until the reaction was complete as indicated by tlc (approximately 1 h). The reaction mixture was poured carefully into iced 1 M aqueous HCl and extracted with three portions of CH2Cl2. The combined extracts were washed wth three portions of aqueous NaHCO3, dried (MgSO4) and the solvent was removed in vacuo to give the crude product. After chromatography (petroleum ether:ethyl acetate, 9: 1) there was obtained 0.140 g (86%) of indole 41 as a white solid. Recrystallization from hexanes/ethyl acetate gave the analytical sample: m.p. 207-208 C.; 1H NMR (300 MHz, CDCl3) delta 0.90 (t, J=7.3 Hz, 3H), 1.81-1.88 (m, 2H), 2.78 (s, 3H), 4.03 (t, J=7.0 Hz, 2H), 7.37-7.38 (m, 5H), 7.48-7.59 (m, 3H), 8.09 (d, J=8.2 Hz, 1H), 8.27 (d, J=8.2 Hz, 1H), 8.52-8.54 (m, 1H); 13C NMR (75.5 MHz, CDCl3) delta 11.3, 19.7, 23.1, 48.7, 109.9, 117.6, 122.7, 122.9, 123.5, 124.2, 125.5, 125.8, 126.1, 126.3, 126.6, 127.0, 130.9, 132.8, 136.6, 137.0, 137.5, 137.9, 192.2; Anal. Calcd for C23H21NO: C, 84.37; H, 6.46; N, 4.28; Found: C, 84.25; H, 6.46; N, 4.30.
With thionyl chloride; In dichloromethane; for 4h;Reflux; Inert atmosphere; 4-Methyl-l-napthoyl chloride[0151] To a solution of 0.35 g (1.89 mmol) of 4-methyl-l-napthoic acid in 3 mL of dry dichloromethane under argon, was added 2.5 ml (34.3 mmol) of thionyl chloride. The solution was refluxed for 4 hrs and the solvent and excess thionyl chloride were removed by vacuum distillation to give a red oil, which was used without further purification.
With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 2h; Step B: 4-Methylnaphthalenecarbonyl chloride.; Step B: 4-Methylnaphthalenecarbonyl chloride. Oxalyl chloride (0.53 niL, 6.1 mmol), followed by anhydrous DMF (2-3 drops) was added to a stirred solution of 4-methylnaphthalenecarboxylic acid (0.227 g, 1.22 mmol) in CH2Cl2 (10 mL). The mixture was stirred at room temperature for 2 h, evaporated and dried under vacuum for 0.5 h. to give the title acid chloride , which was used without further purification in step A.
With thionyl chloride; Step B. 2-(4-Methyl-l-naphthalenyl)-4H-pyrido [3,2-d] [1,3]oxazin-4-one; Following the procedure for Step B in Example 1, a suspension of 3-amino-2- pyridinecarboxylic acid (414 mg, 3.0 mmol) in CH2Cl2 (10 mL) and DIPEA (1.25 mL, 7.2 mmol) was treated with 4-methyl-l-naphthalenecarbonyl chloride, prepared from 4- methyl-1-naphthalenecarbonylic acid (590 mg, 3.17 mmol) with thionyl chloride (4.11 g, 35 mmol), and then with HATU (1.25 g, 3.3 mmol) in DMF (10 mL). The title compound was formed and directly used in Step A.

  • 2
  • [ 6933-49-9 ]
  • [ 87700-67-2 ]
  • 9-(4-methylnaphthalene-1-carbonyl)-9H-carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
16% With caesium carbonate; In N,N-dimethyl-formamide; for 16h;Inert atmosphere; General procedure: Under Ar, a solution of carbazole (5.0g, 29.9mmol), bromoethane (4.45mL, 35.9mmol), and Cs2CO3 (14.6g, 44.8mmol) in DMF (20mL) was stirred at 80C for 16h. The reaction mixture was cooled, diluted with EtOAc (50mL), and filtered. The organic solvents were evaporated in vacuo. The resultant dark oil was purified by column chromatography on silica gel using heptanes/EtOAc in different proportions to afford the title compound as a light-yellow oil (5.075g, 87%).
 

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