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Chemical Structure| 24719-09-3 Chemical Structure| 24719-09-3

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Chemical Structure| 24719-09-3

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Product Details of [ 24719-09-3 ]

CAS No. :24719-09-3
Formula : C5H6N4O2
M.W : 154.13
SMILES Code : O=C(C1=NC=CN=C1N)NO
MDL No. :MFCD10698852

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Application In Synthesis of [ 24719-09-3 ]

* 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 [ 24719-09-3 ]

[ 24719-09-3 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 6761-52-0 ]
  • [ 59046-72-9 ]
  • [ 24719-09-3 ]
  • [ 37993-76-3 ]
YieldReaction ConditionsOperation in experiment
52%; 91% With iodine; In dimethyl sulfoxide; at 100℃;Catalytic behavior; General procedure: General procedure for the syntheses of 2-arylisoquinoline derivatives 4 3-Aminopyrazine-2-carbohydrazide (1, 77mg, 0.5mmol) 2-(arylethynyl) benzaldehydes 2 (0.5mmol), iodine (13mg, 0.05mmol), and DMSO (5.0mL) was added into a dry 25mL flask. The reaction mixture was stirred at 100C for 4-10h until all the 1 and intermediate product hydrazone were consumed which was monitored by TLC. The separation and purification of the products 4 were the same to those of 3. In the process of 4a, the filtrate was extracted with ethyl acetate (30mL*3). The organic layer was combined and dried by anhydrous Na2SO4. The ethyl acetate was recovered by rotary evaporation, and the residue was purified by column chromatography using ethyl acetate and petroleum ether (2:1) as an eluant to give 3-amino-N-hydroxypyrazine-2-carboxamide (8) in 52% yield. 4.2.1 3-Phenylisoquinoline (4a) M.p. 104-105C (Lit.20 103-104C); 1H NMR (CDCl3, 400MHz): deltaH 7.39-7.44 (m, 1H, ArH), 7.49-7.59 (m, 3H, ArH), 7.66-7.70 (m, 1H, ArH), 7.86 (d, J=8.0Hz, 1H, ArH), 7.98 (d, J=8.4Hz, 1H, ArH), 8.06 (s, 1H, ArH), 8.11-8.14 (m, 2H, ArH), 9.33 (s, 1H, ArH). 13C NMR (CDCl3, 100MHz): deltaC 116.5, 126.9, 127.0, 127.1, 127.6, 127.8, 128.5, 128.8, 130.5, 136.7, 139.6, 151.3, 152.4. IR (KBr): nu 2912, 1625, 1585, 1562, 1515, 1489, 1332, 1279, 1196, 1139, 1131, 1035, 960, 944, 884, 742, 713, 680cm-1. HRMS (APCI, m/z): Calcd for C15H12N [M+ H]+ 206.0964, found 206.0973. 4.2.2 3-Amino-N-hydroxypyrazine-2-carboxamide (8) M.p. 198-200C (Lit.21 196C), 1H NMR (DMSO-d6, 400MHz): deltaH 7.42 (brs, 3H, NH2+OH), 7.76 (d, J=2.4Hz, 1H, ArH), 8.17 (d, J=2.4Hz, 1H, ArH), 9.43 (brs, 1H, NH). 13C NMR (DMSO-d6, 100MHz): deltaC 126.3, 131.3, 146.8, 155.1, 163.6.
 

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