4-PYRIDINECARBOXALDEHYDE, 2-CHLORO-5-NITRO- synthesis

3synthesis methods

Product Name:4-PYRIDINECARBOXALDEHYDE, 2-CHLORO-5-NITRO-
CAS Number:946136-72-7
Molecular formula:C6H3ClN2O3
Molecular Weight:186.55

(E)-2-(2-chloro-5-nitropyridin-4-yl)-N,N-dimethylethenamine

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4-PYRIDINECARBOXALDEHYDE, 2-CHLORO-5-NITRO-

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Yield: 71%

Reaction Conditions:

with sodium periodate in tetrahydrofuran;water at 20; for 6 h;

Steps:

1 Synthesis of 2-chloro-5-nitroisonicotinaldehyde
To a solution of (E)-2-(2-chloro-5-nitropyridin-4-yl)-N,N-dimethylethenamine (1.0 equiv) in 1:1 THF/H₂O (0.1 M) was added sodium periodate (3.0 equiv) portionwise. The resulting solution was stirred at rt for 6 hours, at which time the white solid was filtered and rinsed with ethyl acetate. The entire filtrate was washed with NaHCO_3(sat.), with NaCl_(sat.), dried over MgSO₄, filtered and concentrated. Purification by column chromatography (20% ethyl acetate/hexanes, R_f=0.3) yielded 2-chloro-5-nitroisonicotinaldehyde (71%). ¹H NMR (CDCl₃): δ 10.51 (s, 1H), 9.25 (s, 1H), 7.75 (s, 1H).

References:

Burger, Matthew;Lindvall, Mika US2011/195980, 2011, A1 Location in patent:Page/Page column 12

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References

23056-33-9 Synthesis

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References