Methanol → HCID 178486902, compound

HRID 2391740Notes

Reaction equation

HRID 2391740 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([NH2:9])[C:6]([N+:10]([O-])=O)=[CH:5][N:4]=1.[CH3:13]O>[Pd]>[CH3:1][O:2][C:3]1[N:4]=[CH:5][C:6]2[N:10]=[CH:13][NH:9][C:7]=2[CH:8]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 147626984-Amino-2-methoxy-5-nitropyridine

Product 1

HCID 178486902HCID 178486902, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of 15.51 g of 2-methoxy-5-nitropyridin-4-amine (example E7) in 1.55 I methanol was treated with 4.65 g Pd/C (10% Pd) and hydrogenated for 12 h under atmospheric pressure. The reaction mixture was filtered through a plug of CELITE® (diatomaceous earth) and the filtrate was concentrated under vacuum. The resulting residue was treated with 181 ml formic acid and the mixture was refluxed for 50 h. The formic acid was distilled off and the residue was repeatedly purified by flash chromatography (neutral alumina oxide, ethyl acetate/methanol) to yield the title compound.

Workup

  1. filtrationThe reaction mixture was filtered through a plug of CELITE® (diatomaceous earth)
  2. concentrationthe filtrate was concentrated under vacuum
  3. additionThe resulting residue was treated with 181 ml formic acid
  4. temperaturethe mixture was refluxed for 50 h
  5. distillationThe formic acid was distilled off
  6. customthe residue was repeatedly purified by flash chromatography (neutral alumina oxide, ethyl acetate/methanol)

Sources & evidence

ORD record
ord-27bcb2a5bc1c4039ac9641ce91c8049e
Source dataset
uspto-grants-2012_09
Patent number
US08273890B2

Reaction notes

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