Resorcinol → HCID 86747847, compound

HRID 1033486Notes

Reaction equation

HRID 1033486 reaction equation
[CH3:1][N:2]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[C:8]2[C:7](Cl)=[C:6]([Cl:18])[CH:5]=[C:4]([Cl:19])[C:3]1=2.[C:20]1([CH:27]=[CH:26][CH:25]=[C:23](O)[CH:22]=1)[OH:21].C(=O)([O-])[O-].[K+].[K+].CN1C(=O)CCC1>O.O1CCCC1.C1(C)C=CC=CC=1>[Cl:18][C:6]1[CH:5]=[C:4]([Cl:19])[C:3]2[N:2]([CH3:1])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:16])[C:8]=2[C:7]=1[C:23]1[CH:25]=[CH:26][CH:27]=[C:20]([OH:21])[CH:22]=1

Participants

6

Reactant 4

HCID 5054ResorcinolHCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 86747848HCID 86747848, compound

Product 1

HCID 86747847HCID 86747847, compound

Reagents, catalysts & solvents 1

HCID 86683494HCID 86683494, compoundSolvent

Procedure

8 g (25.6 mmol) of N-methyl-1,2,4-trichloroacridone, 8.46 g (76.8 mmol) of resorcinol, 14.15 g (102.4 mmol) of potassium carbonate and 80 ml of NMP are stirred at 60° C. for 30 hours. The mixture is discharged into water/tetrahydrofuran/toluene. The organic phase is washed with water, dried over sodium sulfate, filtered through silica gel and evaporated. The residue is chromatographed on silica gel using methylene chloride. The fractions containing the product are evaporated, and the residue is recrystallized from o-dichlorobenzene. Yield: 5.45 g (55%), melting point 220°-222° C.

Workup

  1. washThe organic phase is washed with water
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered through silica gel
  4. customevaporated
  5. customThe residue is chromatographed on silica gel
  6. additionThe fractions containing the product
  7. customare evaporated
  8. customthe residue is recrystallized from o-dichlorobenzene

Sources & evidence

ORD record
ord-2f53533288ad429290464db0104e9af0
Source dataset
uspto-grants-1994_05
Patent number
US05310909

Reaction notes

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