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

HRID 2358527Notes

Reaction equation

HRID 2358527 reaction equation
[CH3:1][C:2]1[N:11]=[C:10]2[C:5]([C:6](O)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:15]>>[Cl:15][C:6]1[CH:7]=[CH:8][N:9]=[C:10]2[C:5]=1[CH:4]=[CH:3][C:2]([CH3:1])=[N:11]2

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1784229567-methyl-8H-1,8-naphthyridin-4-one

Product 1

HCID 122663725-Chloro-2-methyl-1,8-naphthyridineYield 90%

Conditions

Temperature
50 °C

Procedure

A mixture of the product from Example 1c (320 mg, 2.0 mmol) in 6 mL of POCl3 was heated at 50° C. with stirring for 6 h. Cooled to room temperature and quenched by pouring into ice. Adjusted to pH 10 with NH4OH and extracted with CH2Cl2. Dried over Na2SO4, filtered and concentrated under vacuum giving the title compound as a tan solid (322 mg, 90%).

Workup

  1. temperatureCooled to room temperature
  2. customquenched
  3. additionby pouring into ice
  4. extractionAdjusted to pH 10 with NH4OH and extracted with CH2Cl2
  5. dry with materialDried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ff71d89db47f443288f515436af903ad
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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