Phosphorus oxybromide → HCID 18759599, compound

HRID 432552Notes

Reaction equation

HRID 432552 reaction equation
O[C:2]1[C:15]2[C:6](=[C:7]3[C:12](=[CH:13][CH:14]=2)[C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:10][CH:9]=[N:8]3)[N:5]=[CH:4][C:3]=1C(O)=O.C1(C2C3C(N=CC=2)=C2C(C(O)=CC=N2)=CC=3)C=CC=CC=1.P(Br)(Br)([Br:48])=O.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[Br:48][C:2]1[C:15]2[C:6](=[C:7]3[C:12](=[CH:13][CH:14]=2)[C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:10][CH:9]=[N:8]3)[N:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 24613Phosphorus oxybromideHCID 516892Sodium BicarbonateHCID 178516356HCID 178516356, compoundHCID 178524707HCID 178524707, compound

Product 1

HCID 18759599HCID 18759599, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
260 °C

Procedure

4-Hydroxy-7-phenyl-1,10-phenanthroline-3-carboxylic acid is de-carboxylated in three gram amounts by heating at 250-270° C. in a Woods metal bath until effervescence ceases. A cake, principally comprising 7-phenyl-1,10-phenanthrolin-4-ol, cracks away from the sides of the beaker and is ground up in a mortar. This material is treated with excess phosphoryl bromide (15 mL) and the mixture is heated to 140° C. for 8 hrs. The reaction mixture is cooled to room temperature, and the remaining phosphoryl bromide is distilled off under reduced pressure to yield a semi-crystalline mass. This solid is stirred into a mixture of toluene and dilute sodium bicarbonate sufficient to make the mixture slightly basic. The mixture is stirred for several hours, after which time the toluene layer is separated and the aqueous layer is extracted with additional toluene. The toluene fractions are combined, treated with decolorizing charcoal, filtered, and evaporated to yield the desired product, which is collected by filtration and re-crystallized from toluene.

Workup

  1. temperaturethe mixture is heated to 140° C. for 8 hrs
  2. temperatureThe reaction mixture is cooled to room temperature
  3. distillationthe remaining phosphoryl bromide is distilled off under reduced pressure
  4. customto yield a semi-crystalline mass
  5. customafter which time the toluene layer is separated
  6. extractionthe aqueous layer is extracted with additional toluene
  7. additiontreated with decolorizing charcoal
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-0dad8861c9424930a7e8773898769baf
Source dataset
uspto-grants-2003_12
Patent number
US06664111B2

Reaction notes

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