Phosphorus oxychloride → HCID 19785041, compound

HRID 256519Notes

Reaction equation

HRID 256519 reaction equation
[NH:1]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[N:8][C:9](O)=[C:10]([CH3:16])[C:11]=2[CH3:15])[N:6]=1)C(C)=O.P(Cl)(Cl)([Cl:20])=O>>[NH2:1][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[N:8][C:9]([Cl:20])=[C:10]([CH3:16])[C:11]=2[CH3:15])[N:6]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178474036HCID 178474036, compound

Product 1

HCID 19785041HCID 19785041, compoundYield 92%

Procedure

34.6 g (0.15 mol) of 2-acetamino-7-hydroxy-5,6-dimethyl-1,8-naphthyridine and 380 ml of phosphorus oxychloride are boiled under reflux for 30 minutes, the starting material dissolving. Excess POCl3 is distilled off, the residue poured onto ice and concentrated hydrochloric acid is added. After the mixture has been boiled under reflux for 30 minutes, it is made alkaline with 50% strength sodium hydroxide solution. The precipitate is suction filtered and recrystallized from 4 liters of methanol. There is obtained 28.7 g (92%) of a pale brown solid which is further reacted without any purification.

Workup

  1. temperatureunder reflux for 30 minutes
  2. dissolutionthe starting material dissolving
  3. distillationExcess POCl3 is distilled off
  4. additionthe residue poured onto ice and concentrated hydrochloric acid
  5. additionis added
  6. temperatureunder reflux for 30 minutes
  7. filtrationfiltered
  8. customrecrystallized from 4 liters of methanol

Sources & evidence

ORD record
ord-5f9dd4d2f84e4eb98197d3b5f4a21e48
Source dataset
uspto-grants-1993_11
Patent number
US05258356

Reaction notes

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