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[ CAS No. 42087-81-0 ]

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Chemical Structure| 42087-81-0
Chemical Structure| 42087-81-0
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CAS No. :42087-81-0 MDL No. :MFCD04038813
Formula : C8H6ClNO4 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :215.59 g/mol Pubchem ID :12187125
Synonyms :

Safety of [ 42087-81-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 42087-81-0 ]

  • Upstream synthesis route of [ 42087-81-0 ]
  • Downstream synthetic route of [ 42087-81-0 ]

[ 42087-81-0 ] Synthesis Path-Upstream   1~4

  • 1
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  • [ 77820-58-7 ]
YieldReaction ConditionsOperation in experiment
79% With iron; acetic acid In ethanol at 20℃; for 2 h; Heating / reflux Methyl 2-amino-3-chlorobenzoate. Iron powder (1.94 g, 34.8 mmol) was added to the solution of methyl 3-chloro-2-nitrobenzoate (2.5 g, 111.6 mmol) in EtOH/HOAc (100 mL/100 mL) at room temperature, and then the suspension was refluxed under N2 for 2 hrs. After cooling down to room temperature, partial of the solvents was removed on rotary vacuum, the resulting residue was partitioned between H2O/EtOAc (200 mL/300 mL). The separated organic phase was washed with aqueous NaOH (1N, 50 mL), brine (50 mL), dried over MgSO4, and concentrated on rotary vacuum to afford the expected product as a tan oil (1.7 g, 79percent yield) which became wax type solid standing on bench. The crude product was pure enough to be used in next step without further purification; 1H NMR (400 MHz, CDCl3) δ ppm 3.86 (s, 3H), 6.25 (s, 2H), 6.57 (t, J=7.93 Hz, 1H), 7.39 (dd, J=7.81, 1.51 Hz, 1H), 7.79 (dd, J=8.06, 1.51 Hz, 1H); Mass spec. 185.95 (MH+), Calc. for C8H8ClNO2 185.02.
79%
Stage #1: With iron; acetic acid In ethanol at 20℃; for 2 h; Heating / reflux
Stage #2: With sodium hydroxide In water; ethyl acetate
Methyl 2-amino-3-chlorobenzoate; Iron powder (1.94 g, 34.8 mmol) was added to the solution of methyl 3-chloro-2-nitrobenzoate (2.5 g, 11.6 mmol) in EtOH/HOAc (100 mL/100 mL) at room temperature, and then the suspension was refluxed under N2 for 2 hrs. After cooling down to room temperature, partial of the solvents was removed on rotary vacuum, the resulting residue was partitioned between H2O/EtOAc (200 mL/300 mL). The separated organic phase was washed with aqueous NaOH (1N, 50 mL), brine (50 mL), dried over MgSO4, and concentrated on rotary vacuum to afford the expected product as a tan oil (1.7 g, 79percent yield) which became wax type solid standing on bench. The crude product was pure enough to be used in next step without further purification; 1H NMR (400 MHz, CDCl3) δ ppm 3.86 (s, 3 H), 6.25 (s, 2 H), 6.57 (t, J=7.93 Hz, 1 H), 7.39 (dd, J=7.81, 1.51 Hz, 1 H), 7.79 (dd, J=8.06, 1.51 Hz, 1 H); Mass spec. 185.95 (MH+), Calc. for C8H8ClNO2 185.02.
Reference: [1] Patent: US2006/94707, 2006, A1, . Location in patent: Page/Page column 64
[2] Patent: US2007/259850, 2007, A1, . Location in patent: Page/Page column 99
[3] Bioorganic and Medicinal Chemistry, 1999, vol. 7, # 8, p. 1743 - 1754
  • 2
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  • [ 22233-52-9 ]
YieldReaction ConditionsOperation in experiment
94% With diisobutylaluminium hydride In dichloromethane at -78℃; for 0.25 h; Example 116; This example concerns the synthesis of Aldehyde 12: To a stirred solution of 81 (2.91 g, 13.5 mmol) and CH2Cl2 (134 mL) at -78°C was added DIBAL-H (16.0 mL, 16.0 mmol, 1.0 M in CH2Cl2) over 15 min. After an additional 10 min, the reaction was quenched with MeOH (1.0 mL) and warmed to rt. Next, a solution of aq. sodium potassium tartrate (190 mL, 10percent w/v) was added and vigorously stirred. After 4 h, the reaction mixture was diluted with CH2Cl2 (50 mL) and washed with H2O (3 x 100 mL) and sat. aq. NaCl (100 mL). The dried extract (MgSO4) was concentrated in vacuo and purified by recrystallization with EtOAc / Hexanes (1 :3) to give known aldehyde 12 (2.32 g, 12.7 mmol, 94percent) as a white crystalline solid. 1H NMR (400 MHz, CDCl3) δ 9.90 (s, IH), 7.92 (dd, J= 1.4, 7.7 Hz, IH), 7.80 (dd, J= 1.4, 8.1 Hz, IH), 7.67 (dd, J= 7.7, 8.1 Hz, IH); 13C NMR (100 MHz, CDCl3) δ 186.0, 148.1 136.0, 131.7, 130.1, 128.5, 126.6.
Reference: [1] Journal of Organic Chemistry, 2007, vol. 72, # 26, p. 9857 - 9865
[2] Patent: WO2008/156656, 2008, A2, . Location in patent: Page/Page column 44; 181
[3] Tetrahedron, 2008, vol. 64, # 5, p. 856 - 865
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  • [ 90407-11-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 15, p. 5031 - 5034
  • 4
  • [ 2365-48-2 ]
  • [ 42087-81-0 ]
  • [ 33851-23-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 7, p. 2162 - 2177
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 15, p. 5031 - 5034
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