Sodium Hydroxide → 5,6-Dihydro-8-methoxy-2-(quinolin-2-ylmethylthio)-4H-imidazo-[4,5,1-ij]quinoline

HRID 256308Notes

Reaction equation

HRID 256308 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:23]3=[C:24]([NH:26][C:27](=[S:28])[N:22]3[CH2:21][CH2:20][CH2:19]2)[CH:25]=1.[OH-].[Na+]>CCO>[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:23]3=[C:24]([N:26]=[C:27]([S:28][CH2:3][C:4]4[CH:13]=[CH:12][C:11]5[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=5)[N:5]=4)[N:22]3[CH2:21][CH2:20][CH2:19]2)[CH:25]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 30838232-(Chloromethyl)quinoline hydrochlorideHCID 135032135,6-dihydro-8-methoxy-2-mercapto-4H-imidazo[4,5,1-ij]quinoline

Product 1

HCID 135032105,6-Dihydro-8-methoxy-2-(quinolin-2-ylmethylthio)-4H-imidazo-[4,5,1-ij]quinolineYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Chloromethylquinoline hydrochloride (0.845 g, 4.0 mmol) was added to a solution of 5,6-dihydro-8-methoxy-4H-imidazo[4,5,1-ij]quinoline-2(1H)-thione (0.871 g, 4.0 mmol) in 1 N-NaOH (8 ml) and EtOH (8 ml). The mixture was heated to reflux, cooled to room temperature, concentrated in vacuo, and the aqueous residue extracted with CH2Cl2 (50 ml). The extract was washed with 1NNaOH (2×30 ml), and brine (20 ml), dried (MgSO4), and evaporated in vacuo to give an oil which was purified by chromatography (SiO2, Et2O) and trituration with Et2O-petrol ether to give the title compound (0.885 g, 62%) as yellow crystals, mp 89°-91° C. (Found: C,70.1; H,5.4; N,11.4; C21H19N3OS requires C,69.8; H,5.3; N,11.6%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. concentrationconcentrated in vacuo
  4. extractionthe aqueous residue extracted with CH2Cl2 (50 ml)
  5. washThe extract was washed with 1NNaOH (2×30 ml), and brine (20 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated in vacuo
  8. customto give an oil which
  9. customwas purified by chromatography (SiO2, Et2O) and trituration with Et2O-petrol ether

Sources & evidence

ORD record
ord-8e855320f1a2430bbb493ebb67084ef2
Source dataset
uspto-grants-1987_10
Patent number
US04703044

Reaction notes

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