HCID 54122524, compound → HCID 53921407, compound

HRID 1938349Notes

Reaction equation

HRID 1938349 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[C:8]([CH2:13][N:14]([CH3:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:7]=2>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:21][N:14]([CH2:13][C:8]1[CH:7]=[C:6]2[C:11]([CH:12]=[C:3]([CH:2]=[O:1])[CH:4]=[N:5]2)=[CH:10][CH:9]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 1

HCID 54122524HCID 54122524, compound

Product 1

HCID 53921407HCID 53921407, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

The above 3-hydroxymethyl-7-(methylphenylamino)methylquinoline (306 mg, 1.10 mmol.) was dissolved in dry chloroform (8 mL). To this was added manganese dioxide (0.95 g), and the mixture was stirred overnight at room temperature. The reaction mixture was filtered over Celite®, and the residue was washed with chloroform. The chloroform washings were combined with the filtrate. The solvent was distilled off under reduced pressure, to leave the desired compound as brown oil (222 mg, yield: 73%).

Workup

  1. filtrationThe reaction mixture was filtered over Celite®
  2. washthe residue was washed with chloroform
  3. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-444f72f88c09455fa0d56adbdc446220
Source dataset
uspto-grants-1997_12
Patent number
US05693651

Reaction notes

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