Phosphorus oxychloride → 1,5-Naphthyridine-3-carbonitrile, 4-chloro-6-methyl-

HRID 968713Notes

Reaction equation

HRID 968713 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]([C:12]#[N:13])[C:5]2=O.O=P(Cl)(Cl)[Cl:17]>>[Cl:17][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([CH3:1])[N:3]=2)[N:8]=[CH:7][C:6]=1[C:12]#[N:13]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 587242946-Methyl-4-oxo-1,4-dihydro-1,5-naphthyridine-3-carbonitrile

Product 1

HCID 587242971,5-Naphthyridine-3-carbonitrile, 4-chloro-6-methyl-Yield 57.1%

Procedure

The suspension of 6-methyl-4-oxo-1,4-dihydro-[1,5]naphthyridine-3-carbonitrile (1.47 g, 7.93 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 4-chloro-6-methyl-[1,5]naphthyridine-3-carbonitrile as a brown solid (0.92 g, 57.1%). HR-MS-EI (+) m/e calcd for C10H6ClN3 (M+) 203.0250. found 203.0252.

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-a7b6ed51648248adb4d93116a83bd1b4
Source dataset
uspto-grants-2007_12
Patent number
US07304074B2

Reaction notes

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