Phosphorus oxychloride → 8-Chloro-5-iodo-2-methyl-[1,7]naphthyridine

HRID 1787659Notes

Reaction equation

HRID 1787659 reaction equation
[I:1][C:2]1[C:3]2[CH:4]=[CH:5][C:6]([CH3:13])=[N:7][C:8]=2[C:9](=O)[NH:10][CH:11]=1.P(Cl)(Cl)([Cl:16])=O>>[Cl:16][C:9]1[N:10]=[CH:11][C:2]([I:1])=[C:3]2[C:8]=1[N:7]=[C:6]([CH3:13])[CH:5]=[CH:4]2

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 686207215-Iodo-2-methyl-1,7-naphthyridin-8(7H)-one

Product 1

HCID 576003528-Chloro-5-iodo-2-methyl-[1,7]naphthyridine

Conditions

Temperature
90 °C

Procedure

5-Iodo-2-methyl-7H-[1,7]naphthyridin-8-one (14.2 g, 49.8 mmol) was suspended in phosphorus oxychloride (68 ml, 750 mmol) and stirred for 5 hours at 90° C. The reaction mixture was cooled to room temperature and evaporated to dryness. The residue was taken up in dichloromethane and extracted carefully with saturated NaHCO3-Solution. The aqueous layer was washed two times with dichloromethane. The organic layers were dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (ethyl acetate/heptane 10:90->100:0 gradient). The desired compound was obtained as a light red solid (4.8 g, 32%), MS: m/e=305.0 (M+H+).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customevaporated to dryness
  3. extractionextracted carefully with saturated NaHCO3-Solution
  4. washThe aqueous layer was washed two times with dichloromethane
  5. dry with materialThe organic layers were dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography on silica gel (ethyl acetate/heptane 10:90->100:0 gradient)

Sources & evidence

ORD record
ord-2024d10d3364455091c7b11b5c6900c9
Source dataset
uspto-grants-2009_03
Patent number
US07511055B2

Reaction notes

Loading…