Phosphorus oxychloride → 8-Chloro-2-methyl-1,5-naphthyridine

HRID 968738Notes

Reaction equation

HRID 968738 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2O.O=P(Cl)(Cl)[Cl:15]>>[Cl:15][C:5]1[CH:6]=[CH:7][N:8]=[C:9]2[C:4]=1[N:3]=[C:2]([CH3:1])[CH:11]=[CH:10]2

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1784233686-Methyl-1,5-naphthyridin-4-ol

Product 1

HCID 6013988-Chloro-2-methyl-1,5-naphthyridineYield 67%

Procedure

The suspension of 6-methyl-[1,5]naphthyridin-4-ol (1.60 g, 9.99 mmol) in POCl3 (25 mL) was heated under refluxing for 2 hrs. After cooling to room temperature, the reaction mixture was quenched with ice water and basified with NH4OH followed by extraction with AcOEt. The organic layer was washed with brine and dried over NaSO4, and concentrated to give 8-chloro-2-methyl-[1,5]naphthyridine as a brown solid (1.2 g, 67%). HR-MS-EI (+) m/e calcd for C9H7N2Cl (M+) 178.0298. found 178.0297.

Workup

  1. temperaturewas heated
  2. temperatureunder refluxing for 2 hrs
  3. customthe reaction mixture was quenched with ice water
  4. extractionfollowed by extraction with AcOEt
  5. washThe organic layer was washed with brine
  6. dry with materialdried over NaSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a158cea1f85541cea529233d3a545bfb
Source dataset
uspto-grants-2007_12
Patent number
US07304074B2

Reaction notes

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