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[ CAS No. 5470-82-6 ]

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2D
Chemical Structure| 5470-82-6
Chemical Structure| 5470-82-6
Structure of 5470-82-6 *Storage: {[proInfo.prStorage]}

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Product Details of [ 5470-82-6 ]

CAS No. :5470-82-6MDL No. :MFCD00168259
Formula : C10H10N2 Boiling Point : 326.2°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :158.20Pubchem ID :231556
Synonyms :

Computed Properties of [ 5470-82-6 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 5470-82-6 ]

Signal Word:DangerClass:9
Precautionary Statements:P261-P264-P270-P272-P273-P280-P301+P312-P302+P352-P321-P330-P333+P313-P363-P391-P501UN#:3077
Hazard Statements:H302-H312-H317-H411-H372Packing Group:
GHS Pictogram:

Application In Synthesis of [ 5470-82-6 ]

  • Downstream synthetic route of [ 5470-82-6 ]

[ 5470-82-6 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 5470-82-6 ]
  • [ 71985-80-3 ]
  • 7,8-dibromo-9-methyl-2-(1-methylpiperidin-4-yl)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinoline hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% 7, 8-dibromo-9-methyl-2-( 1 -methylpiperidin-4-yl)-5 ,6-dihydro-4H-imidazo [4,5,1- ]quinoline hydrochloride (Example 7A)To a 7-methyl-8-nitroquinoline (5g, 26.6 mmol) suspended in ethanol (lOOmL)Raney Nickel was added follow by hydrazine monohydrate (2.5 mL, 79.7 mmol).The reaction mixture was stirred at room temperature for 72 hrs. Then reactionmixture was filtered through Celite, washed by methanol and solvents wereconcentrated under reduced pressure. The crude was purified by columnchromatography (silica gel, dichloromethane/methanol 9:1). 7-Methyl-8- aminoquinoline (1.6 g, 10.3 mmol) and 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) (3.6 g, 20.6 mmol) were added to the suspension of <strong>[71985-80-3]1-methyl-4-piperidine carboxylic acid hydrochloride</strong> (1.8 g, 10.3 mmol) and N-methyl morpholine (3.4 mL,30.1 mmol) in acetonitrile (8OmL). The reaction mixture was stirred at 40C for 24 hours. After cooled down to the ambient temperature the solvent was removed under reduced pressure. The residue was purified by colunm chromatography (silica gel, dichloromethane/methanolltriethylamine 8:2:0.1) to gave amide as a white solid. To the amide (1.9 g, 6.7 mmol) dissolved in acetic acid (1 5mL) platinum oxide (0.15 g,0.67 mmol) was added. The reaction was carried out in Parr apparatus under hydrogen atmosphere for 72 hours. Next the reaction mixture was filtered through Celite and washed with methanol. The filtrate was concentrated under reduced pressure. The product was purified by flash chromatography (silica gel, dichloromethane/methanolltriethylamine 9:1:0.2). To the suspension of obtained product (1.6 g, 5.8 mmol) in acetonitrile (7OmL) N-bromosuccinimide (2.3 g, 12.9 mmol) was added. The reaction mixture was stirred at room temperature for 15minutes. The solvent was concentrated under reduced pressure and residue was purified by preparative HPLC. Then the product was dissolved in methanol and 4M HC1 in dioxane was added. The reaction was stirred at room temperature overnight. The white precipitate was filtered off and washed by diethyl ether. The 7,8,9- tribromo-2-( 1 -methylpiperidin-4-yl)-5 ,6-dihydro-4H-imidazo[4,5, 1 -]quinolinehydrochloride (1.3 g)was obtained as a white solid; yield 52%. LC-MS (m/z) 491.8 (M+1); 1H NMR (600 MHz, DMSO) oe 10.70 (s, 1H), 4.31 -4.25 (m, 2H), 3.55 (d, J = 11.5 Hz, 2H), 3.11 (q, J= 12.4 Hz, 2H), 2.95 -2.91 (m, 2H), 2.77 (d, J= 4.7 Hz, 3H), 2.69 (s, 3H), 2.33 -2.25 (m, 2H), 2.24 -2.20 (m, 2H), 2.18 (d, J 13.9 Hz,2H).
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