Hydride → 5-Nitropyridine-2-carbaldehyde

HRID 43074Notes

Reaction equation

HRID 43074 reaction equation
[H-].C([O:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][N:8]=1)=O)C>C(Cl)Cl>[N+:13]([C:10]1[CH:11]=[CH:12][C:7]([CH:5]=[O:4])=[N:8][CH:9]=1)([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 166653HydrideHCID 45116302Ethyl 5-nitropicolinate

Product 1

HCID 151455015-Nitropyridine-2-carbaldehydeYield 49.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

Diisobutylaluminiumo hydride (1 M in DCM, 44 mL, 44 mmol, 1.3 equiv) was added dropwise to a cold (−78° C.) solution of 5-nitro-pyridine-2-carboxylic acid ethyl ester (step 39.4) (6.56 g, 33.5 mmol) in DCM (130 mL), under an argon atmosphere. The reaction mixture was allowed to warm to 5° C., quenched by addition of an aqueous solution of potassium sodium tartrate, diluted with DCM and H2O, stirred for 16 h at rt, and filtered through a pad of celite. The filtrate was extracted several times with DCM. The organic phase was washed with H2O and brine, dried (Na2SO4), filtered and concentrated. The residue was purified by by silica gel column chromatography (EtOAc/Hex, 1:1) to provide 2.54 g of the title compound as a beige solid: ESI-MS: 151.1 [M−H]−.

Workup

  1. customquenched by addition of an aqueous solution of potassium sodium tartrate
  2. additiondiluted with DCM and H2O
  3. filtrationfiltered through a pad of celite
  4. extractionThe filtrate was extracted several times with DCM
  5. washThe organic phase was washed with H2O and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by by silica gel column chromatography (EtOAc/Hex, 1:1)

Sources & evidence

ORD record
ord-b1ef0f95d2f54f5da771592b97516bf2
Source dataset
uspto-grants-2013_09
Patent number
US08536175B2

Reaction notes

Loading…