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[ CAS No. 21901-29-1 ]

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2D
Chemical Structure| 21901-29-1
Chemical Structure| 21901-29-1
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Product Details of [ 21901-29-1 ]

CAS No. :21901-29-1MDL No. :MFCD00047443
Formula : C6H7N3O2 Boiling Point : 309.1°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :153.14Pubchem ID :226028
Synonyms :

Computed Properties of [ 21901-29-1 ]

TPSA : 84.7 H-Bond Acceptor Count : 4
XLogP3 : 1.3 H-Bond Donor Count : 1
SP3 : 0.17 Rotatable Bond Count : 0

Safety of [ 21901-29-1 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P280-P305+P351+P338-P310UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 21901-29-1 ]

  • Upstream synthesis route of [ 21901-29-1 ]
  • Downstream synthetic route of [ 21901-29-1 ]

[ 21901-29-1 ] Synthesis Path-Upstream   1~21

  • 1
  • [ 21901-29-1 ]
  • [ 39745-39-6 ]
  • [ 56057-19-3 ]
Reference: [1] Journal of the American Chemical Society, 1947, vol. 69, p. 63,66
[2] Journal of Heterocyclic Chemistry, 1996, vol. 33, # 6, p. 1815 - 1821
[3] Journal of the American Chemical Society, 1947, vol. 69, p. 63,66
[4] Journal of Heterocyclic Chemistry, 1996, vol. 33, # 6, p. 1815 - 1821
  • 2
  • [ 21901-29-1 ]
  • [ 56057-19-3 ]
Reference: [1] Journal of the American Chemical Society, 1952, vol. 74, p. 3828,3830
[2] Patent: EP2366691, 2011, A1,
  • 3
  • [ 1824-81-3 ]
  • [ 21901-29-1 ]
YieldReaction ConditionsOperation in experiment
29%
Stage #1: at 0℃; for 12 h;
Stage #2: Cooling with ice
Example 7: Synthesis of the 6-(1-ethyleneimine)-2-carbamoyl-3-nitropyridine (compound V) [Show Image] The reagents used was ( i ) HNO3/H2SO4; (ii) NaNO2; (iii) POCl3; (iv) Na2Cr2O7; (v) SOCl2, followed by NH4OH; (vi) aziridine.Synthesis of the compound 24 A concentrated sulphuric acid (100 mL) was cooled in an ice bath, the starting material compound 23 (30 g, 0.28 mol) was slowly added and cooled to 0°C, 42 mL of a mixture in volumetric ratio of 1:1 of a concentrated sulphuric acid (98percent) and a concentrated nitric acid (72percent) was slowly added, and the reaction was run at 0°C for 1h and left standing for 12 h. The reaction liquid was poured into 2 L of ice-water mixture, adjusted to pH=7 by adding strong aqua, and filtered. The filter cake was dried, yielding 54 g of the crude product. The above mixture was subject to wet distillation, resulting in a bright yellow liquid, and it was extracted with ethyl acetate and recrystallized in ethanol to obtain 12.5 g of the compound 24 with a melting point of 156.5-158.5°C (ethyl acetate) and a yield of 29percent.
22%
Stage #1: at -15 - 20℃; for 2 h;
Stage #2: With sodium hydroxide In water
25.0 g (231 mmol) of 2-amino-6-picoline was cooled to -15(C, and dissolved very carefully in concentrated sulfuric acid (100 ml). This solution was cooled to 0(C, and 22.0 ml (60 percent, d = 1.42, 347 mmol) of nitric acid was added dropwise thereto. After the addition, the ice-water bath was removed, and after the heat generation was stopped, the reaction mixture was stirred at room temperature for 2 hours. Thereactionmixture was poured into ice (400 g), and the mixture was controlled to have pH of from 4 to 5 with aqueous 4 N sodium hydroxide solution added thereto. The precipitate formed was taken out through filtration, and washed with hot water. This was dried, and applied to a silica gel column chromatography. From the eluate with chloroform/methanol (50/1, v/v), 7.60 g (22 percent) of the entitled compound was obtained as a yellow solid.1H-NMR(DMSO-d6)δ: 2.37(3H, s), 6.61(1H, d, J=8.7Hz), 7.86(2H, brs), 8.24(1H, d, J=8.7Hz).
Reference: [1] Journal of Medicinal Chemistry, 1996, vol. 39, # 6, p. 1331 - 1338
[2] Patent: EP2366691, 2011, A1, . Location in patent: Page/Page column 11
[3] Bioorganic and Medicinal Chemistry Letters, 1998, vol. 8, # 22, p. 3171 - 3176
[4] Patent: EP1479681, 2004, A1, . Location in patent: Page 122
[5] Patent: US2002/32187, 2002, A1,
  • 4
  • [ 19346-45-3 ]
  • [ 21901-29-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2018, vol. 61, # 8, p. 3309 - 3324
  • 5
  • [ 1824-81-3 ]
  • [ 21901-29-1 ]
Reference: [1] Patent: US5977101, 1999, A,
  • 6
  • [ 1824-81-3 ]
  • [ 22280-62-2 ]
  • [ 21901-29-1 ]
Reference: [1] Journal of Fluorine Chemistry, 2011, vol. 132, # 8, p. 541 - 547
[2] Archiv der Pharmazie, 1995, vol. 328, # 3, p. 247 - 255
[3] Archiv der Pharmazie, 1995, vol. 328, # 3, p. 247 - 255
[4] Yakugaku Zasshi, 1952, vol. 72, p. 434[5] Chem.Abstr., 1953, p. 6404
[6] Journal of the American Chemical Society, 1955, vol. 77, p. 3154
[7] Journal of the American Chemical Society, 1947, vol. 69, p. 63,66
[8] Journal of Molecular Structure, 2013, vol. 1043, p. 15 - 27
  • 7
  • [ 2802-09-7 ]
  • [ 71090-35-2 ]
  • [ 21901-29-1 ]
Reference: [1] Liebigs Annalen der Chemie, 1986, # 2, p. 380 - 383
  • 8
  • [ 2802-09-7 ]
  • [ 92277-16-2 ]
  • [ 21901-29-1 ]
Reference: [1] Liebigs Annalen der Chemie, 1986, # 2, p. 380 - 383
  • 9
  • [ 109-06-8 ]
  • [ 21901-29-1 ]
Reference: [1] Journal of the American Chemical Society, 1947, vol. 69, p. 63,66
  • 10
  • [ 2802-08-6 ]
  • [ 71090-35-2 ]
  • [ 21901-29-1 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1996, vol. 33, # 6, p. 1815 - 1821
  • 11
  • [ 1824-81-3 ]
  • [ 22280-62-2 ]
  • [ 25864-34-0 ]
  • [ 21901-29-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 11, p. 2987 - 2991
  • 12
  • [ 33986-37-7 ]
  • [ 21901-29-1 ]
Reference: [1] Acta Chimica Hungarica, 1986, vol. 121, # 4, p. 333 - 338
[2] Acta Chimica Hungarica, 1986, vol. 121, # 4, p. 333 - 338
  • 13
  • [ 33986-37-7 ]
  • [ 7664-93-9 ]
  • [ 22280-62-2 ]
  • [ 21901-29-1 ]
Reference: [1] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1920, vol. 50, p. 536[2] Chem. Zentralbl., 1923, vol. 94, # III, p. 1022
  • 14
  • [ 21901-29-1 ]
  • [ 39745-40-9 ]
Reference: [1] Journal of the American Chemical Society, 1947, vol. 69, p. 63,66
  • 15
  • [ 22280-62-2 ]
  • [ 39745-39-6 ]
  • [ 21901-29-1 ]
  • [ 28489-45-4 ]
Reference: [1] Patent: US6011029, 2000, A,
  • 16
  • [ 1824-81-3 ]
  • [ 22280-62-2 ]
  • [ 21901-29-1 ]
Reference: [1] Journal of Fluorine Chemistry, 2011, vol. 132, # 8, p. 541 - 547
[2] Archiv der Pharmazie, 1995, vol. 328, # 3, p. 247 - 255
[3] Archiv der Pharmazie, 1995, vol. 328, # 3, p. 247 - 255
[4] Yakugaku Zasshi, 1952, vol. 72, p. 434[5] Chem.Abstr., 1953, p. 6404
[6] Journal of the American Chemical Society, 1955, vol. 77, p. 3154
[7] Journal of the American Chemical Society, 1947, vol. 69, p. 63,66
[8] Journal of Molecular Structure, 2013, vol. 1043, p. 15 - 27
  • 17
  • [ 1824-81-3 ]
  • [ 22280-62-2 ]
  • [ 25864-34-0 ]
  • [ 21901-29-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 11, p. 2987 - 2991
  • 18
  • [ 33986-37-7 ]
  • [ 7664-93-9 ]
  • [ 22280-62-2 ]
  • [ 21901-29-1 ]
Reference: [1] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1920, vol. 50, p. 536[2] Chem. Zentralbl., 1923, vol. 94, # III, p. 1022
  • 19
  • [ 21901-29-1 ]
  • [ 39745-39-6 ]
YieldReaction ConditionsOperation in experiment
77% at 0℃; for 16 h; Synthesis of the compound 25 The compound 24 (10g, 0.065 mol) was added into 100 mL of water, a concentrated sulphuric acid (12 mL) was slowly added with agitation and cooled to 0 °C in an ice bath. Sodium nitrite (6.9 g, 0.098 mol) was added in batches, reacted at 0°C for 4h, and left standing for 12 h. A large amount of yellow precipitate was precipitated, filtrated under the reduced pressure, vacuum-dried to obtain 7.7 g of a yellow product with a yield of 77percent. The melting point is 216.5-218.5°C (water).
Reference: [1] Patent: EP2366691, 2011, A1, . Location in patent: Page/Page column 11
[2] Journal of the American Chemical Society, 1952, vol. 74, p. 3828,3830
  • 20
  • [ 21901-29-1 ]
  • [ 39745-39-6 ]
  • [ 56057-19-3 ]
Reference: [1] Journal of the American Chemical Society, 1947, vol. 69, p. 63,66
[2] Journal of Heterocyclic Chemistry, 1996, vol. 33, # 6, p. 1815 - 1821
[3] Journal of the American Chemical Society, 1947, vol. 69, p. 63,66
[4] Journal of Heterocyclic Chemistry, 1996, vol. 33, # 6, p. 1815 - 1821
  • 21
  • [ 21901-29-1 ]
  • [ 353277-27-7 ]
Reference: [1] Patent: EP2366691, 2011, A1,
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