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

HRID 256306Notes

Reaction equation

HRID 256306 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:5]=1.[CH3:16][O:17][C:18]1[CH:19]=[C:20]2[C:25]3=[C:26]([NH:28][C:29](=[S:30])[N:24]3[CH2:23][CH2:22][CH2:21]2)[CH:27]=1.[OH-].[Na+]>C(O)C>[CH3:16][O:17][C:18]1[CH:19]=[C:20]2[C:25]3=[C:26]([N:28]=[C:29]([S:30][CH2:3][C:4]4[CH:9]=[CH:8][CH:7]=[C:6]([C:10]5[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=5)[N:5]=4)[N:24]3[CH2:23][CH2:22][CH2:21]2)[CH:27]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 135032135,6-dihydro-8-methoxy-2-mercapto-4H-imidazo[4,5,1-ij]quinolineHCID 199011562-Chloromethyl-6-phenylpyridine hydrochloride

Product 1

HCID 135032075,6-Dihydro-8-methoxy-2-[(6-phenylpyridin-2-yl)-methylthio]-4H-imidazo[4,5,1-ij]quinoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Chloromethyl-6-phenylpyridine hydrochloride 1.942 g, 8.1 mmol) was added to a solution of 5,6-dihydro-8-methoxy-4H-imidazo[4,5,1-ij]quinoline-2[1H]-thione (1.78 g, 8.1 mmol) in ethanol (16 ml) and 1N-sodium hydroxide (16.2 ml). The mixture was heated under reflux for 15 seconds and cooled to room temperature. The ethanol was removed by evaporation in vacuo and the aqueous mixture extracted with dichloromethane (2×150 ml). The extracts were dried (MgSO4) and evaporated in vacuo to give a brown solid which was recrystallised from MeOH to give the title compound as the quarter hydrate (2.77 g, 88%), mp 134°-135° C. (Found: C, 70.5; H, 5.8; N, 10.4; C23H21N3OS1/4H2O requires C, 70.5; H, 5.5; N, 10.7%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 15 seconds
  3. customThe ethanol was removed by evaporation in vacuo
  4. extractionthe aqueous mixture extracted with dichloromethane (2×150 ml)
  5. dry with materialThe extracts were dried (MgSO4)
  6. customevaporated in vacuo
  7. customto give a brown solid which
  8. customwas recrystallised from MeOH

Sources & evidence

ORD record
ord-31386b8b23594ff7ae6794e70eea2862
Source dataset
uspto-grants-1987_10
Patent number
US04703044

Reaction notes

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