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[ CAS No. 152684-26-9 ]

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Chemical Structure| 152684-26-9
Chemical Structure| 152684-26-9
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CAS No. :152684-26-9 MDL No. :MFCD00834963
Formula : C6H5BrN2O3 Boiling Point : 334.6°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :233.02 g/mol Pubchem ID :817774
Synonyms :

Safety of [ 152684-26-9 ]

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

Application In Synthesis of [ 152684-26-9 ]

  • Upstream synthesis route of [ 152684-26-9 ]
  • Downstream synthetic route of [ 152684-26-9 ]

[ 152684-26-9 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 152684-26-9 ]
  • [ 42409-58-5 ]
YieldReaction ConditionsOperation in experiment
99%
Stage #1: for 2.5 h;
Stage #2: With sodium carbonate In water; ethyl acetate
A 3-neck I -L flask was fitted with a heating mantle, temperature controller, and an overhead stirrer. To the reaction flask was added 2-nitro-3'"iethoxy-5-bromopyridine 2 (37.5 g 0.16 mol), acetic acid (600 ml), and iron powder ( 18.9 g, 0.34 mol), and the resulting mixture was stirred and heated at 80 0C for 2.5 h. The reaction was deemed complete by LCMS and allowed to cool to rt. The reaction mixture was filtered through Celite and the filter cake was washed with acetic acid, and the combined filtrate and washings were concentrated. The resulting residue was partitioned between saturated aqueous Na2CO3 solution (400 mi) and EtOAc (400 ml) and the layers separated. The organic phase was washed with brine (200 mL), dried (Na>=SC^), filtered, and concentrated to afford 32.5 g (0.16 mol, 99 percent yield) of a tan solid as 2-amino-3-methoxy-5- bromopyridine:1H NMR (300 MHz, DMSO^fe) δ pom 7.56 (d, ./= 2.1 Hz, 1 H), 7.17 (d, ./ = 2.1 Hz, 1 H), 5.93 (br s, 2 H), 3.79 (s, 3 H); LCMS m/s (MH+) 203.0, /R - 0.34 min.
Reference: [1] Patent: WO2010/100127, 2010, A1, . Location in patent: Page/Page column 69-70
  • 2
  • [ 50720-12-2 ]
  • [ 152684-26-9 ]
YieldReaction ConditionsOperation in experiment
85% With sulfuric acid; nitric acid In water at 0℃; for 20 h; The compound (20.91 g, 0.11 mol) obtained in Step 1 was dissolved in concentrated sulfuric acid (63 ml), nitric acid (5.2 ml, 0.12 mol) was added under ice-cooling, and the mixture was stirred for 20 hr. The reaction mixture was gently poured into ice water and the mixture was stirred. The precipitated solid was filtered and washed with water. The obtained solid was dissolved in ethyl acetate, and the solution was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure to give the object product as a pale-yellow solid (21.97 g, yield 85percent). 1H NMR(CDCl3 400 MHz) (δ) ppm: 4.01 (3H, s), 7.68 (1H, d, J=1.6 Hz), 8.16 (1H, d, J=1.9 Hz)
76%
Stage #1: at 20℃;
Stage #2: at 0 - 20℃;
Stage #3: With sodium carbonate In water; ethyl acetate
To a cooled flask containing 3-methoxy-5-bromopyridine I (39,8 g, 0.21 mol) was slowly added concentrated H2SO4 (120 ml) with the reaction mixture temperature maintained below 20 °C. The resulting mixture was stirred unitl homogeneity. The reaction mixture was cooled to 0-5 ftC and 90percent I INO3 (16>;5 g, 0.24 moi) was added dropwise while maintaining constant temperature. The resulting reaction mixture was stirred for 24 h, at ambient temperature. The reaction was deemed complete (<;5percent of 1 by HPLC) and the reaction mixture was poured onto ice (400 g), then partitioned with EtOAc (400 ml). The layers were separated and (he organic phase was sequentially washed with saturated aqueous Na2CO3 solution (400 ml), water (400 ml) and brine (400 ml), dried overNa2SO-i) Tillered, and concentrated under reduced pressure to furnish a pale yellow solid (45.8 g) as crude product. The material was recrystallized from MTBE (175 mL) and the crystals were harvested, washed with cold MTBK (80 mL-), and dried under high vacuum to give 22.7 g of yellow soiM as product. The mother liquor and filtraie were combined, concentrated, and recrystoellized from MTBE (35 mL) gave 6.3 g of pure product, The remaining mother liquor and filtrates were combined and concentrated. The resulting residue was purified by silica gel chromatography, eluting with a slow gradient of hexanes-EtOAc (hexanes, 4:1 hexancs-EtOAc) to give 8.5 g of product, Λ combined total of 37.5 g (0.16 mol, 76percent yield) of a yellow crystalline solid was obtained as 2-nitro-3 -methoxy-5 -bromopyridine:1H NMR (30Q MHz, CDCl3) 6 8.16 (d, J.(TM). 1.9 Hz, 1 H), 7.68 (d, J = 1.6 Hz, 1 H), 4.01 (s, 3 H); IXMS m/z (MH') 232.9, /R 0.73 min.
Reference: [1] Patent: US2006/84665, 2006, A1, . Location in patent: Page/Page column 70
[2] Patent: WO2010/100127, 2010, A1, . Location in patent: Page/Page column 69-70
[3] Acta Chemica Scandinavica, 1993, vol. 47, # 8, p. 805 - 812
[4] Recueil des Travaux Chimiques des Pays-Bas, 1955, vol. 74, p. 1171,1174
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  • [ 625-92-3 ]
  • [ 152684-26-9 ]
Reference: [1] Acta Chemica Scandinavica, 1993, vol. 47, # 8, p. 805 - 812
[2] Recueil des Travaux Chimiques des Pays-Bas, 1955, vol. 74, p. 1171,1174
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