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

HRID 250130Notes

Reaction equation

HRID 250130 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](=[CH:26][CH:27]=1)[CH:24]=[N:23][C:22]([NH2:28])=[CH:21]2>ClCCl>[N:28]([C:22]1[N:23]=[CH:24][C:25]2[C:20]([CH:21]=1)=[CH:19][C:18]([CH3:17])=[CH:27][CH:26]=2)=[C:1]=[S:2]

Participants

4

Reactant 2

HCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 187279006-Methylisoquinolin-3-amine

Product 1

HCID 574766053-Isothiocyanato-6-methylisoquinolineYield 47.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 1,1′-thiocarbonyldipyridin-2(1H)-one (220 mg, 0.948 mmol) in dichloromethane (10 mL) at ambient temperature was added 6-methylisoquinolin-3-amine (125 mg, 0.790 mmol). The reaction mixture was placed into a preheated oil-bath and stirred at 40° C. for 18 h, then removed from the oil-bath and cooled to ambient temperature. The mixture was concentrated and the crude material was purified by silica gel chromatography (5-30% ethyl acetate in hexanes) to afford 3-isothiocyanato-6-methylisoquinoline (75 mg, 0.375 mmol, 47.4% yield), as an off-white solid. 1H NMR (400 MHz, CDCl3) δ ppm 9.03 (s, 1H), 7.88 (d, J=8.24 Hz, 1H), 7.56 (s, 1H), 7.46 (dd, J=8.24, 1.53 Hz, 1H), 7.39 (s, 1H) 2.57 (s, 3H). MS (LC/MS) R.T.=1.92; [M+H]+=201.13.

Workup

  1. customThe reaction mixture was placed into a preheated oil-bath
  2. customremoved from the oil-bath
  3. temperaturecooled to ambient temperature
  4. concentrationThe mixture was concentrated
  5. customthe crude material was purified by silica gel chromatography (5-30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-1a945c0cb3c643b1a0b37047bf6304d5
Source dataset
uspto-grants-2011_01
Patent number
US07863291B2

Reaction notes

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