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CAS No. : | 366452-97-3 | MDL No. : | MFCD09701290 |
Formula : | C8H6N2O3 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | RTDDSWLIZLMORY-UHFFFAOYSA-N |
M.W : | 178.14 | Pubchem ID : | 21961387 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With ammonium formate In methanol at 35℃; for 2 h; | A mixture of 4-nitro-2,3-dihydro-lH-isoindol-l-one (2Og), ammonium formate (35g) and 7.5percent Pd/C( 0.6g) in methanol (60ml) was stirred for 2 hours by heating up to 35°C . Pd/C was filtered and the filtrate concentrated under reduced pressure. The residue was recrystallized from water to give 15.3g of light yellow solid, yield: 92percent. mp: 195.6-197°C .1H-NMR: (300MHz, DMSO-dβ) δ: 4.3 l(s, 2H), 6.76(d, IH), 7.14(t, IH), 6.86(d, IH), 5.30(s, 2H), 8.26(s, IH)1H-NMR: (300MHz, DMSO-dβ/ D2O) δ: 4.14(s, 2H), 6.79(d, IH), 6.93(d, IH), 7.16(t, IH)FAB(M+1): 149 Element analysis: theoretical data: C 64.85percent, H 5.44percent, N 18.91percent measured data: C 64.96percent, H 5.61percent, N 19.02percent Test condition of HPLC: type and specification of column: phenomenex Luna 5u Cl 8250mmχ4.6mm; velocity: l .Oml/min; λ=230nm mobile phase: acetonitrile/0.1percentphosphate = 15/85 or acetonitrile/O.OIMammonium acetate = 10/90 appearance time of tar get yield: 3.580minutes ; 4.790minutes purity of target yield: 99.66percent |
83% | With ammonium formate In N,N-dimethyl-formamide | d Synthesis of 4-amino-2,3-dihydro-1H-isoindol-1-one (4): To a solution of 4-nitro-2,3-dihydro-1H-isoindol-1-one (compound 3, 3.2 gm, 0.018 mmol.) in DMF (10 ml), was added ammonium formate (5.750 gm), and Pd-C (100 mg), and the reaction mixture was stirred at 100° C. for 30 min. The mixture was then filtered through a pad of celite, and the celite was washed with DMF (10 ml) and water (10 ml). The filtrate was concentrated under vacuum to give compound 4 (2.2 gm, 83percent). 1NMR (DMSO-D6): 4.20 (s, 2H, CH2), 5.20 (bs, NH2), 6.82 (dd,1H, Ar-H), 7.02 (dd,1H, Ar-H), 7.16 (t,1H, Ar-H), 8.20 (bs,1H). |
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