Sodium Iodide → 7-Nitro-3-(6-nitroquinol-2-ylmethyl)-1,2,4,5-tetrahydro-3H-3-benzazepine

HRID 620734Notes

Reaction equation

HRID 620734 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH2:12][C:6]=2[CH:5]=1)([O-:3])=[O:2].Cl[CH2:16][C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[C:22]([N+:27]([O-:29])=[O:28])[CH:23]=2)[N:18]=1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N+:1]([C:4]1[CH:14]=[CH:13][C:7]2[CH2:8][CH2:9][N:10]([CH2:16][C:17]3[CH:26]=[CH:25][C:24]4[C:19](=[CH:20][CH:21]=[C:22]([N+:27]([O-:29])=[O:28])[CH:23]=4)[N:18]=3)[CH2:11][CH2:12][C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 113100427-Nitro-2,3,4,5-tetrahydro-1H-benzo[D]azepineHCID 126651392-(Chloromethyl)-6-nitroquinoline

Product 1

HCID 212450597-Nitro-3-(6-nitroquinol-2-ylmethyl)-1,2,4,5-tetrahydro-3H-3-benzazepine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

7-Nitro-1,2,4,5-tetrahydro-3H-3-benzazepine (0.35 g), 2-chloromethyl-6-nitroquinoline (0.4 g - see Chem. Pharm. Bull, 28, page 2441 [1980]), sodium iodide (0.27 g) and potassium carbonate (0.25 g) in acetonitrile were heated under reflux for 18 hours. The solvent was then removed in vacuo, the residue dissolved in methylene chloride and washed three times with aqueous sodium carbonate and twice with brine. The organic layer was dried (Na2SO4) and evaporated in vacuo to give an oil which was triturated with hexane to give the title compound, yield 0.61 g, m.p. 127°-130°.

Workup

  1. temperatureunder reflux for 18 hours
  2. customThe solvent was then removed in vacuo
  3. dissolutionthe residue dissolved in methylene chloride
  4. washwashed three times with aqueous sodium carbonate
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. customevaporated in vacuo
  7. customto give an oil which
  8. customwas triturated with hexane

Sources & evidence

ORD record
ord-9c92243ec6ab486190a3bb8c80477519
Source dataset
uspto-grants-1989_04
Patent number
US04822793

Reaction notes

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