Phosphorus oxychloride → HCID 12818606, compound

HRID 67951Notes

Reaction equation

HRID 67951 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:18])[N:8]([CH3:17])[C:9]2[C:14]([C:15]=1O)=[CH:13][CH:12]=[CH:11][N:10]=2)=[O:5])[CH3:2].P(Cl)(Cl)([Cl:21])=O>>[Cl:21][C:15]1[C:14]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[N:8]([CH3:17])[C:7](=[O:18])[C:6]=1[C:4]([O:3][CH2:1][CH3:2])=[O:5]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 54696179Ethyl 4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate

Product 1

HCID 12818606HCID 12818606, compound

Procedure

A stirred mixture of 1.7 g. of 4-hydroxy-1,2-dihydro-1-methyl-2-oxo-1,8-naphthyridine-3-carboxylic acid ethyl ester in 25 ml. of phosphorus oxychloride was heated under reflux for 2 hours. The phosphorus oxychloride was removed in a rotary evaporator and the residue was poured into 100 ml. of ice water. The precipitate which formed was collected, air dried and a small amount of the 1.9 g. was recrystallized from heptane twice to give the analytical sample of the title compound, m.p. 132°-135° C.

Workup

  1. additionA stirred mixture of 1.7 g
  2. temperatureunder reflux for 2 hours
  3. customThe phosphorus oxychloride was removed in a rotary evaporator
  4. additionthe residue was poured into 100 ml
  5. customThe precipitate which formed
  6. customwas collected
  7. customair dried
  8. customwas recrystallized from heptane twice

Sources & evidence

ORD record
ord-0a4817e376ba4d748879be6d600dbe11
Source dataset
uspto-grants-1982_08
Patent number
US04347362

Reaction notes

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