3-Nitrosalicylic acid → HCID 22613708, compound

HRID 636357Notes

Reaction equation

HRID 636357 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:6]([C:7]([OH:9])=O)[C:5]=1[OH:13])([O-:3])=[O:2].[F:14][C:15]1[C:16]([O:28][C:29]2[CH:34]=[CH:33][C:32]([NH2:35])=[CH:31][CH:30]=2)=[N:17][CH:18]=[N:19][C:20]=1[O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.P(Cl)(Cl)Cl>C1(C)C=CC=CC=1>[F:14][C:15]1[C:16]([O:28][C:29]2[CH:34]=[CH:33][C:32]([NH:35][C:7](=[O:9])[C:6]3[CH:10]=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[C:5]=3[OH:13])=[CH:31][CH:30]=2)=[N:17][CH:18]=[N:19][C:20]=1[O:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 68073-Nitrosalicylic acidHCID 24387Phosphorus trichlorideHCID 22613707HCID 22613707, compound

Product 1

HCID 22613708HCID 22613708, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 1.7 g (9 mmol) of 3-nitrosalicylic acid and 2.7 g (9 mmol) of 4-(5-fluoro-6-phenoxy-pyrimidin-4-yloxy)-phenylamine in 20 ml of toluene is heated with stirring to 50° C. 0.5 g of phosphorus trichloride is added, and the mixture is heated at the boil under reflux for a further 4 hours. After cooling, the mixture is concentrated and the residue is extracted with dichloromethane. The organic phase is washed repeatedly with water and dried over sodium sulphate. The solvent is distilled off, giving 1.7 g (41% of theory) of N-[4-(5-fluoro-6-phenoxy-pyrimidin-4-yloxy)-phenyl]-2-hydroxy-3-nitrobenzamide.

Workup

  1. temperatureis heated
  2. temperaturethe mixture is heated at the boil
  3. temperatureunder reflux for a further 4 hours
  4. temperatureAfter cooling
  5. concentrationthe mixture is concentrated
  6. extractionthe residue is extracted with dichloromethane
  7. washThe organic phase is washed repeatedly with water
  8. dry with materialdried over sodium sulphate
  9. distillationThe solvent is distilled off

Sources & evidence

ORD record
ord-52dc3fad4fdc4f719d729b42d8318ae1
Source dataset
uspto-grants-2001_02
Patent number
US06194418B1

Reaction notes

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