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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
ノート
印刷プレビュー

反応式

HRID 2103087 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180
Acetone
溶媒

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-144dd9c0664f4b8ca09c7e8d206f9959
出典データセット
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07576094B2

反応ノート

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