2-Dimethylaminopyridine → 6-Isothiocyanato-4,5,8-trimethylquinoline

HRID 1598648Notes

Reaction equation

HRID 1598648 reaction equation
[NH2:1][C:2]1[C:3]([CH3:14])=[C:4]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[CH3:13].C1C=C(O[C:22](OC2N=CC=CC=2)=[S:23])N=CC=1.CN(C1C=CC=CN=1)C>C(Cl)Cl>[N:1]([C:2]1[C:3]([CH3:14])=[C:4]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[CH3:13])=[C:22]=[S:23]

Participants

5

Reactant 3

HCID 218852-DimethylaminopyridineHCID 719784O,O-Dipyridin-2-yl carbonothioateHCID 153800186-Amino-4,5,8-trimethylquinoline

Product 1

HCID 153800196-Isothiocyanato-4,5,8-trimethylquinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 6-amino-4,5,8-trimethylquinoline (0.37 g), di-2-pyridyl thionocarbonate (0.494 g) (DPT) (Aldrich), dimethylaminopyridine (0.052 g) and methylene chloride (4 mL) is stirred at room temperature for 2 hours. An additional 100 mg of DPT is added, and stirring is continued for one hour. Another 100 mg portion of DPT is added, and the reaction is stirred at room temperature for one more hour. The mixture is concentrated by evaporation and purified by chromatography through a short column consisting of layers of sand/flash silica gel/sand, using 20% ethyl acetate in hexane as the eluting solvent, providing 6-isothiocyanato-4,5,8-trimethylquinoline.

Workup

  1. additionAn additional 100 mg of DPT is added
  2. stirringstirring
  3. waitis continued for one hour
  4. additionAnother 100 mg portion of DPT is added
  5. stirringthe reaction is stirred at room temperature for one more hour
  6. concentrationThe mixture is concentrated by evaporation
  7. custompurified by chromatography through a short column

Sources & evidence

ORD record
ord-0f5e211c40924b1d8b4a341520cfaca9
Source dataset
uspto-grants-1998_04
Patent number
US05739148

Reaction notes

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