Selenium Dioxide → 3-Phenyl-1,7-naphthyridine-5-carboxaldehyde

HRID 2379700Notes

Reaction equation

HRID 2379700 reaction equation
[CH3:1][C:2]1[CH:11]=[N:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:6]=[N:7]2.[Se](=O)=[O:19]>C1C2C(=CC=CC=2)C=CC=1.C(Cl)Cl>[C:12]1([C:5]2[CH:6]=[N:7][C:8]3[CH:9]=[N:10][CH:11]=[C:2]([CH:1]=[O:19])[C:3]=3[CH:4]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 24007Selenium DioxideHCID 100821995-Methyl-3-phenyl-1,7-naphthyridine

Product 1

HCID 103539863-Phenyl-1,7-naphthyridine-5-carboxaldehyde

Reagents, catalysts & solvents 2

HCID 931NaphthaleneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
200 °C

Procedure

36.2 g (164 mmol) of the compound from Example III are well stirred with 27.4 g of selenium dioxide in 130 g of naphthalene at 180° C. After 5 h, a further 3.65 g of SeO2 are added and the mixture is stirred for a further 3 h at 200° C. It is allowed to cool and is dissolved in CH2Cl2 and the solution is concentrated on a rotary evaporator after addition of 200 g of silica gel. The residue is applied to a large silica gel column and chromatographed (toluene→ethyl acetate). Yield: 18 g (47%) M.p.: 148° C.

Workup

  1. temperatureto cool
  2. concentrationthe solution is concentrated on a rotary evaporator
  3. additionafter addition of 200 g of silica gel
  4. customchromatographed (toluene→ethyl acetate)

Sources & evidence

ORD record
ord-b9d425255d104b6b8412ffb94c9ba21b
Source dataset
uspto-grants-1994_11
Patent number
US05364855

Reaction notes

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