Phosphoric Acid → 2h-Indol-2-one,1,3-dihydro-5-methoxy-1-phenyl-

HRID 1510078Notes

Reaction equation

HRID 1510078 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:7]=[CH:6]2.ClN1C(=[O:24])CCC1=O.P(=O)(O)(O)O>C(Cl)Cl.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:7](=[O:24])[CH2:6]2

Participants

6

Reactant 3

HCID 1004Phosphoric AcidHCID 31398ChlorosuccinimideHCID 136034295-Methoxy-1-phenyl-1H-indole

Product 1

HCID 136034182h-Indol-2-one,1,3-dihydro-5-methoxy-1-phenyl-Yield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

The compound of step 1 (800 mg, 3.58 mmol) was dissolved in DCM (25 ml), and N-chlorosuccinimide (526 mg, 3.94 mmol) was added. The reaction mixture was stir at room temperature overnight. The solvent was removed, the resulting solid was dissolved in concentrated acetic acid (15 ml) and heated to 70° C. After the addition of phosphoric acid (3.04 ml, 44.6 mmol; 85%) the reaction mixture was heated to 130° C. for 2.5 h. The cooled mixture was diluted with water and extracted with EA. The extracts were dried over sodium sulfate, filtered and evaporated. The residue was purified by silica gel chromatography (EA/HEP 1:3). 557 mg of the title compound were obtained.

Workup

  1. customThe solvent was removed
  2. dissolutionthe resulting solid was dissolved in concentrated acetic acid (15 ml)
  3. temperatureheated to 70° C
  4. temperaturewas heated to 130° C. for 2.5 h
  5. extractionextracted with EA
  6. dry with materialThe extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by silica gel chromatography (EA/HEP 1:3)

Sources & evidence

ORD record
ord-3173d6a5fb154556a61310e7d5f20c17
Source dataset
uspto-grants-2012_07
Patent number
US08211885B2

Reaction notes

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