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[ CAS No. 366452-97-3 ]

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Chemical Structure| 366452-97-3
Chemical Structure| 366452-97-3
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Product Details of [ 366452-97-3 ]

CAS No. :366452-97-3 MDL No. :MFCD09701290
Formula : C8H6N2O3 Boiling Point : 488.8°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :178.14 g/mol Pubchem ID :21961387
Synonyms :

Safety of [ 366452-97-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 366452-97-3 ]

  • Upstream synthesis route of [ 366452-97-3 ]
  • Downstream synthetic route of [ 366452-97-3 ]

[ 366452-97-3 ] Synthesis Path-Upstream   1~3

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YieldReaction ConditionsOperation 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).
Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 1, p. 248 - 253[2] Angew. Chem., 2017, vol. 129, # 1, p. 254 - 259,6
[3] Patent: WO2010/139266, 2010, A1, . Location in patent: Page/Page column 38-39
[4] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 81 - 85
[5] Patent: US2002/95044, 2002, A1,
[6] Patent: WO2006/12374, 2006, A1, . Location in patent: Page/Page column 209-210
[7] Patent: US2003/225106, 2003, A1, . Location in patent: Page 93
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YieldReaction ConditionsOperation in experiment
90% With ammonia In methanol at 20℃; for 2.5 h; A mixture of methyl 2-bromomethyl-3-nitrobenzoate (2Og) and methanol (200ml) was stirred under ammonia gas for 30 min at room temperature, and was kept in heat preservation for 2 hours. Crystal grew in an ice bath for 2 hours, and then filtered, and dried to give 11.7g of light yellow crystal, yield: 90percent. mp: 235.4~236.7°C .1H-NMR: (300MHz, DMSO-dβ) δ: 4.78(s, 2H), 7.79(t, IH), 8.10(d, IH), 8.41(d, IH), 8.90(S, IH).1H-NMR: (300MHz, DMSO-dβ/EhO) δ: 4.76(s, 2H), 7.77(t, IH), 8.08(d, IH), 8.39(d, IH). FAB(M+1): 179 Element analysis: theoretical data: C 53.94percent, H 3.39percent, N 15.72percent measured data: C 54.08percent, H 3.49percent, N 15.81percent Test condition of HPLC: type and specification of column: phenomenex Luna 5u Cl 8250mmχ4.6mm; velocity: l .Oml/min; λ=230nm mobile phase: acetonitrile /0.1percent phosphate = 30/70 appearance time of target yield : 5.810 minutes purity of target yield: 99.59percent
Reference: [1] Patent: WO2010/139266, 2010, A1, . Location in patent: Page/Page column 37-38
[2] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 81 - 85
[3] Angewandte Chemie - International Edition, 2017, vol. 56, # 1, p. 248 - 253[4] Angew. Chem., 2017, vol. 129, # 1, p. 254 - 259,6
[5] Patent: WO2006/12374, 2006, A1, . Location in patent: Page/Page column 209
[6] Patent: US2002/95044, 2002, A1,
[7] Patent: US2003/225106, 2003, A1, . Location in patent: Page 93
[8] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 2, p. 814 - 819
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 81 - 85
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 2, p. 814 - 819
[3] Angewandte Chemie - International Edition, 2017, vol. 56, # 1, p. 248 - 253[4] Angew. Chem., 2017, vol. 129, # 1, p. 254 - 259,6
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