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Sodium Iodide → 7',8'-dimethyl-1'-(quinolin-2-ylmethyl)-2',3'-dihydro-1'H-spiro[cyclobutane-1,4'-quinolin]-6'-ol

HRID 2103087
Notes
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Reaction equation

HRID 2103087 reaction equation
[CH3:1][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([C:6]3([CH2:15][CH2:14][CH2:13]3)[CH2:7][CH2:8][NH:9]2)=[CH:4][C:3]=1[OH:16].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-])([O-])=O.[K+].[K+].[I-].[Na+]>CC(C)=O>[CH3:1][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([C:6]3([CH2:13][CH2:14][CH2:15]3)[CH2:7][CH2:8][N:9]2[CH2:18][C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]=2)=[CH:4][C:3]=1[OH:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 203942-(Chloromethyl)quinolineHCID 578035137',8'-dimethyl-2',3'-dihydro-1'H-spiro[cyclobutane-1,4'-quinolin]-6'-ol

Product 1

HCID 578034957',8'-dimethyl-1'-(quinolin-2-ylmethyl)-2',3'-dihydro-1'H-spiro[cyclobutane-1,4'-quinolin]-6'-ol

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 7′,8′-dimethyl-2′,3′-dihydro-1′H-spiro[cyclobutane-1,4′-quinolin]-6′-ol (300 mg), 2-(chloromethyl)quinoline (600 mg), K2CO3 (637 mg), and sodium iodide (40 mg) in acetone (50 mL) was refluxed overnight under nitrogen. The reaction mixture was then cooled down and concentrated by evaporation. Distilled water was added to the residue and the aqueous solution was extracted with ethyl acetate (3×20 mL).The organic layer was combined, dried over Na2SO4, and evaporated. The crude compound was purified by column chromatography (2% MeOH in CH2Cl2) yielding 7′,8′-dimethyl-1′-(quinolin-2-ylmethyl)-2′,3′-dihydro-1′H-spiro[cyclobutane-1,4′-quinolin]-6′-ol as an off-white solid. 1H-NMR (300 MHz, CDCl3) δ=8.28 (d, J=6 Hz, 1H); 8.15 (d, J =6 Hz, 1H); 8.05 (d, J=9 Hz, 1H); 7.88 (t, J=6 Hz, 1H); 7.76 (t, J=6 Hz, 1H); 7.02 (s, 1H); 4.21 (s, 2H); 2.99 (m, 2H); 2.35 (m, 2H); 2.24 (s, 3H); 2.20 (s, 3H); 1.99 (m, 6H) ppm. 13C-NMR (75 MHz, CDCl3) δ=161.20; 149.46; 147.54; 139.58; 137.16; 135.93; 131.04; 129.73; 128.54; 127.70; 127.52; 126.18; 122.83; 119.73; 111.48; 92.98; 77.48; 71.26; 68.59; 60.73; 45.03; 43.92; 40.12; 36.74; 29.88; 15.28; 14.79; 12.54 ppm. MS: (m/z)=359 (100, M+H+).

Workup

  1. temperaturewas refluxed overnight under nitrogen
  2. temperatureThe reaction mixture was then cooled down
  3. concentrationconcentrated by evaporation
  4. additionDistilled water was added to the residue
  5. extractionthe aqueous solution was extracted with ethyl acetate (3×20 mL).The organic layer
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customThe crude compound was purified by column chromatography (2% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-144dd9c0664f4b8ca09c7e8d206f9959
Source dataset
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07576094B2

Reaction notes

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