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Acetonitrile → 7-(2-Chloroethoxy)-8-methoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile

HRID 2213802
ノート
印刷プレビュー

反応式

HRID 2213802 の反応式
C([Li])CCC.[C:6](#[N:8])[CH3:7].ClCCO[C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][C:22]=1OC)[CH:19]=[C:18]([C:25](OCC)=O)[C:17](/[N:30]=C/N(C)C)=C2.[Cl:35][CH2:36][CH2:37][O:38][C:39]1[CH:48]=[C:47]2[C:42]([CH:43]=[C:44](/[N:54]=[CH:55]/N(C)C)[C:45]([C:49]([O:51]CC)=O)=[CH:46]2)=[CH:41][C:40]=1[O:59][CH3:60]>O1CCCC1>[N:8]1[C:15]2[C:20](=[CH:21][CH:22]=[CH:13][CH:14]=2)[CH:19]=[C:18]([C:17]#[N:30])[CH:25]=1.[Cl:35][CH2:36][CH2:37][O:38][C:39]1[C:40]([O:59][CH3:60])=[CH:41][C:42]2[CH:43]=[C:44]3[C:45]([C:49](=[O:51])[C:7]([C:6]#[N:8])=[CH:55][NH:54]3)=[CH:46][C:47]=2[CH:48]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 6342AcetonitrileHCID 178418339ButyllithiumHCID 178468532HCID 178468532、化合物HCID 178468534HCID 178468534、化合物

生成物 2

HCID 931773-QuinolinecarbonitrileHCID 116384657-(2-Chloroethoxy)-8-methoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile収率 76%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
-78 °C

実験手順

To 2.5 mL of dry tetrahydrofuran at −78° C. is added 1.8 mL of 2.5 M n-butyllithium (4.4 mmol). Then 0.24 mL of dry acetonitrile in 4.5 mL of dry tetrahydrofuran is added dropwise over 10 minutes. This is stirred and additional 15 minutes at −78° C., then the ethyl 6-(2-chloroethoxy)-3-{[(E)-(dimethylamino)methylidene]-amino}-7-methoxy-2-naphthoate and ethyl 7-(2-chloroethoxy)-3-{[(E)-(dimethylamino)methylidene]amino}-6-methoxy-2-naphthoate (1:1 mixture) is dissolved in 3 mL of tetrahydrofuran and added dropwise over 15 minutes. The reaction mixture is stirred for 30 minutes at −78° C., then quenched with 0.57 mL of glacial acetic acid, and warmed to room temperature. To the yellow mixture is added 10 mL of water. The solids are filtered, washed with water and dried to give 0.502 g of 8-(2-chloroethoxy)-7-methoxy-4-oxo-1,4-dihydrobenzo]quinoline-3-carbonitrile and 7-(2-chloroethoxy)-8-methoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile (1:1 mixture) as a yellow green solid (76%), m.p. 260–73° C. dec.

後処理

  1. additionadded dropwise over 15 minutes
  2. stirringThe reaction mixture is stirred for 30 minutes at −78° C.
  3. customquenched with 0.57 mL of glacial acetic acid
  4. temperaturewarmed to room temperature
  5. additionTo the yellow mixture is added 10 mL of water
  6. filtrationThe solids are filtered
  7. washwashed with water
  8. customdried

出典と根拠

ORDレコード
ord-8747ecffbcf84c2dbd2c5aa5a1a4f561
出典データセット
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07105531B2

反応ノート

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