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

HRID 1901466Notes

Reaction equation

HRID 1901466 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-4,5,8trimethylquinoline (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-16cf537591814b119563adc175d28bab
Source dataset
uspto-grants-1996_11
Patent number
US05578607

Reaction notes

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