438 JOURNAL OF CHEMICAL RESEARCH 2018
tetramethylsilane (TMS) as an internal standard. Electrospray
ionisation mass spectrometry (ESI-MS) analyses were recorded in
an Agilent 1100 Series MSD Trap SL (Santa Clara, CA, USA). The
reactions were monitored by thin-layer chromatography (TLC; HG/
T2354-92, GF254), and compounds were visualised on TLC with UV
light. HPLC analyses were performed on a Schimadzu LC-20, column,
Shimadzu Inertsil-SP C18 (5 µm; 250 mm × 4.6 mm).
Acknowledgement
This work was financially supported by Liaoning Provincial
Natural Science Foundation of China (No. 201602707).
Electronic Supplementary Information
The ESI associated with this paper can be found at:
Synthesis of methyl hydrazinecarboxylate (3)
Hydrazine hydrate (80%, 188 mL, 3 mol) was added dropwise to a
solution of dimethyl carbonate (281 mL, 3.3 mol) over 1 h at 50 °C.
On the completion of addition, the mixture was stirred at 70 °C for
4 h. Then the mixture was cooled to 0 °C. The precipitate was collected
by filtration, washed with petroleum ether and dried to give compound
3 as a white solid; yield 246 g (91%); m.p. 68–69 °C (lit.29 69–70 °C);
1H NMR (600 MHz, CDCl3): δ 6.10 (br, 1H), 3.77–3.73 (m, 5H).
Received 26 June 2018; accepted 22 July 2018
Paper 1805495
Published online: 15 August 2018
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A stirred and cooled solution of methyl (E)-1-(2-oxopropyl)-2-
(pyridin-3-ylmethylene)hydrazine-1-carboxylate (100 g, 0.4 mol)
and tetrahydrofuran (800 mL) was treated dropwise with 80%
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1
not adjusted to weight %); m.p. 214–216 °C; H NMR (600 MHz,
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