Potassium Carbonate → 2-Chlorodibenzo[f,h]quinoxaline

HRID 330719Notes

Reaction equation

HRID 330719 reaction equation
P(Cl)(Cl)([Cl:3])=O.[N+:6]1([O-])[C:15]2[C:10](=[C:11]3[CH:23]=[CH:22][CH:21]=[CH:20][C:12]3=[C:13]3[CH:19]=[CH:18][CH:17]=[CH:16][C:14]3=2)[N:9]=[CH:8][CH:7]=1.C(=O)([O-])[O-].[K+].[K+]>O>[Cl:3][C:7]1[CH:8]=[N:9][C:10]2[C:15](=[C:14]3[CH:16]=[CH:17][CH:18]=[CH:19][C:13]3=[C:12]3[CH:20]=[CH:21][CH:22]=[CH:23][C:11]3=2)[N:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 58019514Dibenzo[f,h]quinoxaline, 1-oxide

Product 1

HCID 580194962-Chlorodibenzo[f,h]quinoxalineYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Next, 18 mL of phosphoryl chloride was dripped into 2.91 g of dibenzo[f,h]quinoxaline-1-oxide obtained in the above Step 1. This mixed solution was stirred while being heated under reflux for 1 hour. This mixed solution was poured into iced water, followed by addition of potassium carbonate so that the mixture was alkaline. This solution was filtered, and the obtained residue was washed with water and then methanol to give the object of the synthesis (as a pale yellow powder in a yield of 93%). The synthesis scheme of Step 2 is illustrated in the following (a″′-2-2).

Workup

  1. customobtained in the above Step 1
  2. temperaturewhile being heated
  3. temperatureunder reflux for 1 hour
  4. filtrationThis solution was filtered
  5. washthe obtained residue was washed with water
  6. custommethanol to give
  7. customthe object of the synthesis (as a pale yellow powder in a yield of 93%)
  8. customThe synthesis scheme of Step 2

Sources & evidence

ORD record
ord-523b9c4e97b643f8ad5dbfb9b5aeeea5
Source dataset
uspto-grants-2014_11
Patent number
US08877351B2

Reaction notes

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