Water → 7-isothiocyanato-3,4-dihydroquinolin-2(1H)-one

HRID 868894Notes

Reaction equation

HRID 868894 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.[C:13](N1C=CN=C1)(N1C=CN=C1)=[S:14].O>CN(C=O)C>[N:1]([C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1)=[C:13]=[S:14]

Participants

5

Reactant 3

HCID 962WaterHCID 802641,1'-ThiocarbonyldiimidazoleHCID 52002427-amino-3,4-dihydro-1H-quinolin-2-one

Product 1

HCID 157190197-isothiocyanato-3,4-dihydroquinolin-2(1H)-oneYield 85.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 7-amino-3,4-dihydroquinolin-2(1H)-one (0.20 g, 1.2 mmol) in DMF (5.2 mL) was added dropwise to a solution of 1,1′-thiocarbonyldiimidazole (0.22 g, 1.2 mmol) in DMF (2.1 mL) at room temperature over 1 hour. The mixture was stirred for 30 minutes and then water was slowly added. The resulting precipitate was collected by filtration (rinsed with water) and dried under vacuum to afford the title compound (0.21 g, 83% yield), which was used without purification.

Workup

  1. filtrationThe resulting precipitate was collected by filtration (rinsed with water)
  2. customdried under vacuum

Sources & evidence

ORD record
ord-0a46c64344304f5ea687cda9808a595d
Source dataset
uspto-grants-2015_03
Patent number
US08969325B2

Reaction notes

Loading…