Potassium Carbonate → 2,6-Dichloro-1,7-naphthyridine

HRID 485199Notes

Reaction equation

HRID 485199 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][N:11]=1)[NH:8][C:7](=O)[CH:6]=[CH:5]2.O=P(Cl)(Cl)[Cl:15].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[Cl:15][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][N:11]=[C:2]([Cl:1])[CH:3]=2)[N:8]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 155923736-Chloro-1,7-naphthyridin-2(1H)-one

Product 1

HCID 155923742,6-Dichloro-1,7-naphthyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1.08 g (6 mmoles) of 6-chloro-1,7-naphthyridin-2-one and 10 ml of POCl3 were warmed at reflux for one hour to give a clear solution. Upon cooling, a precipitate formed and the mixture was poured cautiously over ice. CH2Cl2 was added and the mixture was neutralized with solid K2CO3. The CH2Cl2 layer was separated and the aqueous layer washed twice with CHCl3. The combined organic layers were washed with water, dried over K2CO3 and evaporated to give a white solid. The solid was recrystallized from hexane/acetone to give 1.14 g (95% of theoretical) of the desired product as short, white needles having a melting point of 213°-216° C. Analysis calculated for C8H4Cl2N2 : C, 48.27; H, 2.03; N, 14.08. Found: C, 48.80; H, 2.09; N, 14.55.

Workup

  1. temperaturewere warmed
  2. temperatureat reflux for one hour
  3. customto give a clear solution
  4. temperatureUpon cooling
  5. customa precipitate formed
  6. additionthe mixture was poured cautiously over ice
  7. customThe CH2Cl2 layer was separated
  8. washthe aqueous layer washed twice with CHCl3
  9. washThe combined organic layers were washed with water
  10. dry with materialdried over K2CO3
  11. customevaporated
  12. customto give a white solid
  13. customThe solid was recrystallized from hexane/acetone

Sources & evidence

ORD record
ord-6501f6af6c494c6fabc989431408cbfd
Source dataset
uspto-grants-1985_08
Patent number
US04536208

Reaction notes

Loading…