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Chemical Structure| 69958-52-7 Chemical Structure| 69958-52-7

Structure of 69958-52-7

Chemical Structure| 69958-52-7

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Product Details of [ 69958-52-7 ]

CAS No. :69958-52-7
Formula : C9H12N2
M.W : 148.21
SMILES Code : NC1=CC2=C(C=N1)CCCC2
MDL No. :MFCD10574676

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Application In Synthesis of [ 69958-52-7 ]

* 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 [ 69958-52-7 ]

[ 69958-52-7 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 25475-67-6 ]
  • [ 69958-52-7 ]
YieldReaction ConditionsOperation in experiment
57% With platinum(IV) oxide; hydrogen; trifluoroacetic acid; for 3h; A mixture of <strong>[25475-67-6]isoquinolin-3-amine</strong> (239 mg, 1.66mmol), platinum(IV)oxide (28mg, 0.123 mmol), and TFA (6mL) was hydrogenated in the Parr apparatus for 3 hrs. Thereaction mixture was filtered with the aid ofethyl acetate. Thefiltrate was evaporated in vacuo and the residue was partitionedbetween 10percent aqueous sodium carbonate and ethylacetate. The layers were separated, the aqueous phase waswashed again with ethyl acetate, and the combined organiclayers were washed with brine and dried over magnesiumsulfate. The drying agent was filtered off and the solventevaporated. The material was purified by colunm chromatographyin ethyl acetate to give 139.8 mg (57percent) 5,6,7,8-tetrahydro<strong>[25475-67-6]isoquinolin-3-amine</strong> as a yellow-white solid.
34% With hydrogen; In ethyl acetate; trifluoroacetic acid; EXAMPLE 64 STR66 3-Amino-5,6,7,8-tetrahydroisoquinoline Using the method of Example 63, Step A, 75 mg of <strong>[25475-67-6]3-aminoisoquinoline</strong> (7.73 mmoles) and 8.7 mg platinum oxide in 2 mL of trifluoroacetic acid was shaken under 40 psi of hydrogen for 3 h. The mixture was filtered and catalyst was washed with ethyl acetate. After concentrating the filtrate, the residue was dissolved in 10 mL of ethyl acetate and washed with 5 mL of saturated aquous sodium bicarbonate. The organic solution was dried (sodium sulfate), decanted, and concentrated to give a yellow syrup. Flash coumn chromatography on 19 g of silica gel, eluding with 600 mL of 50percent ethyl acetate/hexane gave 26.5 mg (34percent yield) of 3-amino-5,6,7,8-tetrahydroisoquinoline as a pale yellow solid. 1 H NMR (400 MHz, CDCl3): delta 7.78 (s, 1H), 6.22 (s, 1H), 4.12 (bs, 2H), 2.65-2.56 (m, 4H), 1.78-1.68 (m, 4H). Mass spectrum (FAB): m/e=149 (M+1)
 

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