Sodium Hydroxide → 5,6-dihydro-2-(quinolin-2-ylmethylthio)-4H-imidazo[4,5,1-ij]quinoline

HRID 256307Notes

Reaction equation

HRID 256307 reaction equation
[NH:1]1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][N:3]3[C:2]1=[S:13].[OH-].[Na+].Cl.Cl[CH2:18][C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=1>C(O)C>[N:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:27]=[CH:28][C:19]=1[CH2:18][S:13][C:2]1[N:3]2[C:12]3[C:7]([CH2:6][CH2:5][CH2:4]2)=[CH:8][CH:9]=[CH:10][C:11]=3[N:1]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 30838232-(Chloromethyl)quinoline hydrochlorideHCID 134578575,6-dihydro-2-mercapto[4H]imidazo [4,5,1-ij]quinoline

Product 1

HCID 135032085,6-dihydro-2-(quinolin-2-ylmethylthio)-4H-imidazo[4,5,1-ij]quinolineYield 55.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5,6-dihydro-4H-imidazo[4,5,1-ij]-quinoline-2(1H)-thione (2.02 g, 11.6 mmol) in ethanol (25 ml) and 1N-sodium hydroxide was treated with 2-(chloromethyl)quinoline hydrochloride (2.48 g, 11.6 mmol) heated to reflux, cooled to room temperature, and the ethanol removed by evaporation in vacuo. The aqueous mixture was filtered and the precipitate washed with water (5×50 ml), dried in vacuo, and recrystallised from cyclohexane - EtOAc to give 5,6-dihydro-2-(quinolin-2-ylmethylthio)-4H-imidazo[4,5,1-ij]quinoline (2.13 g, 55%) as yellow crystals mp 125°-126° C. (Found: C, 72.8; H, 5.3; N,12.4 C20H17N3S requires C, 72.5; H, 5.2; N, 12.7%).

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. customthe ethanol removed by evaporation in vacuo
  4. filtrationThe aqueous mixture was filtered
  5. washthe precipitate washed with water (5×50 ml)
  6. customdried in vacuo
  7. customrecrystallised from cyclohexane - EtOAc

Sources & evidence

ORD record
ord-d6f32f06ec2046bc8777a1bb1141b6b5
Source dataset
uspto-grants-1987_10
Patent number
US04703044

Reaction notes

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