Potassium Phosphate, Tribasic → 6-oxo-5H-phenanthridine-2-carbonitrile

HRID 504012Notes

Reaction equation

HRID 504012 reaction equation
C(O[C:4](=[O:22])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1B1OC(C)(C)CCCCCO1)C.I[C:24]1[CH:30]=[C:29]([C:31]#[N:32])[CH:28]=[CH:27][C:25]=1[NH2:26].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCOCC1>[O:22]=[C:4]1[C:5]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:27]2[CH:28]=[C:29]([C:31]#[N:32])[CH:30]=[CH:24][C:25]=2[NH:26]1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 44163954-Amino-3-iodobenzonitrileHCID 684587052-(4,4-Dimethyl-[1,3,2]dioxaboronan-2-yl)-benzoic acid ethyl ester

Product 1

HCID 167280326-oxo-5H-phenanthridine-2-carbonitrileYield 120.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

2-(4,4-Dimethyl-[1,3,2]dioxaboronan-2-yl)-benzoic acid ethyl ester (19.84 g), 2-iodo-4-cyanoaniline (18.47 g), tetrakis(triphenylphosphine)palladium (8.75 g) and potassium phosphate (35.36 g) were added to dioxane (360 ml), and the resulting mixture was heated under reflux overnight. The reaction solvent was cooled, and the produced solid was collected by filtration, washed with water and dried to thereby obtain 17.3 g (yield: quantitative) of the title compound as a yellow solid.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux overnight
  3. temperatureThe reaction solvent was cooled
  4. filtrationthe produced solid was collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-9ed42e946e2045cab16085505fcca9c0
Source dataset
uspto-grants-2010_08
Patent number
US07777038B2

Reaction notes

Loading…