Phosphorus oxychloride → HCID 13535954, compound

HRID 1583802Notes

Reaction equation

HRID 1583802 reaction equation
P(Cl)(Cl)([Cl:3])=O.O[C:7]1[C:16]([O:17][CH3:18])=[CH:15][C:14]([N+:19]([O-:21])=[O:20])=[C:13]2[C:8]=1[CH:9]=[CH:10][CH:11]=[N:12]2>[OH-].[NH4+]>[Cl:3][C:7]1[C:16]([O:17][CH3:18])=[CH:15][C:14]([N+:19]([O-:21])=[O:20])=[C:13]2[C:8]=1[CH:9]=[CH:10][CH:11]=[N:12]2

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1353992885323-58-0

Product 1

HCID 13535954HCID 13535954, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 14923Ammonium HydroxideSolvent

Procedure

To 150 ml of phosphorus oxychloride, at an internal temperature of 80°-85°, was added in portions, with vigorous stirring, during 0.5 hr, 40.5 g (0.184 mole) of 5-hydroxy-6-methoxy-8-nitroquinoline. After completion of addition, the mixture, which had turned from a red solution to a yellow suspension, was heated under reflux for 1.5 hr. The golden yellow solution was allowed to cool to room temperature and the resulting yellow mush was added to a vigorously stirred mixture of 700 ml of conc ammonium hydroxide and ice. The addition rate was regulated to keep the temperature from rising above 25° The pale yellow precipitate was washed with water and air dried to give 43 g (97%) of 5-chloro-6-methoxy-8-nitroquinoline mp 204°-206° (Mp 204° cited by R. C. Fuson et al., J. Org. Chem., 12, 799 (1947).

Workup

  1. additionAfter completion of addition
  2. temperaturewas heated
  3. temperatureunder reflux for 1.5 hr
  4. customfrom rising above 25°
  5. washwas washed with water and air
  6. customdried

Sources & evidence

ORD record
ord-0eb8476b099d4ef99e440caf76970b62
Source dataset
uspto-grants-1985_11
Patent number
US04554279

Reaction notes

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