1,1'-Thiocarbonyldi-2(1H)-pyridone → 3-Isothiocyanato-6,8-dimethylisoquinoline

HRID 250141Notes

Reaction equation

HRID 250141 reaction equation
[C:1](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:2].[CH3:17][C:18]1[CH:19]=[C:20]2[C:25](=[C:26]([CH3:28])[CH:27]=1)[CH:24]=[N:23][C:22]([NH2:29])=[CH:21]2>ClCCl>[N:29]([C:22]1[N:23]=[CH:24][C:25]2[C:20]([CH:21]=1)=[CH:19][C:18]([CH3:17])=[CH:27][C:26]=2[CH3:28])=[C:1]=[S:2]

Participants

4

Reactant 2

HCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 574766096,8-Dimethylisoquinolin-3-amine

Product 1

HCID 574766103-Isothiocyanato-6,8-dimethylisoquinolineYield 8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 1,1′-thiocarbonyldipyridin-2(1H)-one (1.35 g, 5.8 mmol) in dichloromethane (19 mL) at ambient temperature was added 6,8-dimethylisoquinolin-3-amine (1 g, 5.8 mmol). The reaction mixture was placed into a preheated oil-bath and stirred at 40° C. for 18 h, then cooled, concentrated, and the crude material was purified by silica gel chromatography (10-35% ethyl acetate in hexanes) to afford 3-isothiocyanato-6,8-dimethylisoquinoline (93.7 mg, 0.437 mmol, 8%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 9.20 (s, 1H), 7.36-7.44 (m, 2H), 7.23 (s, 1H), 2.75 (s, 3H), 2.51 (s, 3H). MS (LC/MS) R.T.=2.03; [M+H]+=215.1.

Workup

  1. customThe reaction mixture was placed into a preheated oil-bath
  2. temperaturecooled
  3. concentrationconcentrated
  4. customthe crude material was purified by silica gel chromatography (10-35% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-759a1387f6634b80bfc36fc74ada9fce
Source dataset
uspto-grants-2011_01
Patent number
US07863291B2

Reaction notes

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