Ethyl Acetate → 5-Methoxy-4-nitropicolinaldehyde

HRID 2370870Notes

Reaction equation

HRID 2370870 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N+:11]([O-:13])=[O:12])=[CH:5][C:6]([CH2:9][OH:10])=[N:7][CH:8]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.CCOC(C)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:4]([N+:11]([O-:13])=[O:12])=[CH:5][C:6]([CH:9]=[O:10])=[N:7][CH:8]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 86687998(5-Methoxy-4-nitropyridin-2-yl)methanol

Product 1

HCID 866879995-Methoxy-4-nitropicolinaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (5-methoxy-4-nitropyridin-2-yl)methanol (4 g, 0.021 mol) in DCM (30 mL), was added Dess-Martin Periodinane (18.43 g, 0.043 mol, Spectrochem, India) and reaction was stirred for 3 h at rt. The reaction progress was monitored by TLC (50% EtOAc in petroleum ether). After completion of the reaction, sat'd NaHCO3 (20 mL) was added and the product was extracted with DCM (3×25 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated to give the title compound as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.95 (s, 1H), 9.02 (s, 1H), 8.36 (s, 1H), 4.19 (s, 3H). MS (ESI, positive ion) m/z: 182.9 (M+H).

Workup

  1. additionwas added
  2. extractionthe product was extracted with DCM (3×25 mL)
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1b315b303d464ea1b4a643bfb8aa07bb
Source dataset
uspto-grants-2014_04
Patent number
US08710043B2

Reaction notes

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