Diisobutylaluminumhydride → 5-Nitropyridine-2-carbaldehyde

HRID 2409634Notes

Reaction equation

HRID 2409634 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C([O:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][N:17]=1)=O)C>C(Cl)Cl>[N+:22]([C:19]1[CH:20]=[CH:21][C:16]([CH:14]=[O:13])=[N:17][CH:18]=1)([O-:24])=[O:23]

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 45116302Ethyl 5-nitropicolinate

Product 1

HCID 151455015-Nitropyridine-2-carbaldehydeYield 49.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

Diisobutylaluminium 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-29c6dd1fef93447ca1f5464865fa9179
Source dataset
uspto-grants-2014_08
Patent number
US08815901B2

Reaction notes

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