(E)-2-(2-chloro-5-nitropyridin-4-yl)-N,N-diMethylethenaMine → 2-Chloro-5-nitropyridine-4-carbaldehyde

HRID 1028042Notes

Reaction equation

HRID 1028042 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](/[CH:8]=C/N(C)C)[C:5]([N+:13]([O-:15])=[O:14])=[CH:4][N:3]=1.I([O-])(=O)(=O)=[O:17].[Na+]>C1COCC1.O>[Cl:1][C:2]1[CH:7]=[C:6]([C:5]([N+:13]([O-:15])=[O:14])=[CH:4][N:3]=1)[CH:8]=[O:17]

Participants

4

Reactant 2

HCID 6163756(E)-2-(2-chloro-5-nitropyridin-4-yl)-N,N-diMethylethenaMineHCID 23667635Sodium periodate

Product 1

HCID 469162492-Chloro-5-nitropyridine-4-carbaldehydeYield 71%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

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 NaHCO3(sat.), with NaCl(sat.), dried over MgSO4, filtered and concentrated. Purification by column chromatography (20% ethyl acetate/hexanes, Rf=0.3) yielded 2-chloro-5-nitroisonicotinaldehyde (71%). 1H NMR (CDCl3): δ 10.51 (s, 1H), 9.25 (s, 1H), 7.75 (s, 1H).

Workup

  1. filtrationwas filtered
  2. washrinsed with ethyl acetate
  3. washThe entire filtrate was washed with NaHCO3(sat.), with NaCl(sat.)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by column chromatography (20% ethyl acetate/hexanes, Rf=0.3)

Sources & evidence

ORD record
ord-60b26efbd93b4e4e9a1dd3e16547cd86
Source dataset
uspto-grants-2014_05
Patent number
US08735424B2

Reaction notes

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