Sodium Iodide → 6'-methoxy-5',7'-dimethyl-1'-(quinolin-2-ylmethyl)-3',4'-dihydro-1'H-spiro[cyclobutane-1,2'-quinoline]

HRID 2103088Notes

Reaction equation

HRID 2103088 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:17])=[C:5]2[C:10](=[CH:11][C:12]=1[CH3:13])[NH:9][C:8]1([CH2:16][CH2:15][CH2:14]1)[CH2:7][CH2:6]2.Cl[CH2:19][C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]=1.C([O-])([O-])=O.[K+].[K+].[I-].[Na+]>CC(C)=O>[CH3:1][O:2][C:3]1[C:4]([CH3:17])=[C:5]2[C:10](=[CH:11][C:12]=1[CH3:13])[N:9]([CH2:19][C:20]1[CH:29]=[CH:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=1)[C:8]1([CH2:14][CH2:15][CH2:16]1)[CH2:7][CH2:6]2

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 203942-(Chloromethyl)quinolineHCID 578035566'-methoxy-5',7'-dimethyl-3',4'-dihydro-1'H-spiro[cyclobutane-1,2'-quinoline]

Product 1

HCID 690595946'-methoxy-5',7'-dimethyl-1'-(quinolin-2-ylmethyl)-3',4'-dihydro-1'H-spiro[cyclobutane-1,2'-quinoline]Yield 57.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 6′-methoxy-5′,7′-dimethyl-3′,4′-dihydro-1′H-spiro[cyclobutane-1,2′-quinoline] (270 mg), 2-(chloromethyl)quinoline (626 mg), K2CO3 (528 mg) and sodium iodide (30 mg) in acetone (20 mL) was refluxed over night. After evaporation of the solvent, water was added to the residue and the aqueous solution was extracted with ethyl acetate (3×20 mL). The combined organic layers were dried over Na2SO4 and the solvent was removed by evaporation. The residue was purified by column chromatography (10% ethyl acetate/hexane), giving 6′-methoxy-5′,7′-dimethyl-1′-(quinolin-2-ylmethyl)-3′,4′-dihydro-1′H-spiro[cyclobutane-1,2′-quinoline] as a light yellow solid (250 mg).

Workup

  1. temperaturewas refluxed over night
  2. customAfter evaporation of the solvent, water
  3. additionwas added to the residue
  4. extractionthe aqueous solution was extracted with ethyl acetate (3×20 mL)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. customthe solvent was removed by evaporation
  7. customThe residue was purified by column chromatography (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ff324bebcda14148aef9d5450dd3042d
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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