1,2-Dichloroethane → 2,3-Dihydrothieno[3,2-b]quinolin-9-amine

HRID 248122

反応式

HRID 248122 の反応式
[C:1](#[N:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[S:10]1[CH2:14][CH2:13][C:12](=O)[CH2:11]1.ClCCCl.[OH-].[Na+]>[Cl-].[Cl-].[Zn+2].CC(=O)CC>[NH2:9][C:1]1[C:2]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[N:4]=[C:12]2[CH2:13][CH2:14][S:10][C:11]=12

参加物

7

反応物 4

HCID 111,2-DichloroethaneHCID 14798Sodium HydroxideHCID 61252Dihydro-3(2H)-thiophenoneHCID 729132-Aminobenzonitrile

生成物 1

HCID 143728282,3-Dihydrothieno[3,2-b]quinolin-9-amine収率 31.8%

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 6569Methyl Ethyl Ketone溶媒

実験手順

Anthranilonitrile (4.80 g) and tetrahydrothiophen-3-one (8.17 g) were stirred until a homogeneous mixture was obtained and then freshly fused ZnCl2 (8.0 g) was added and the reaction mixture heated at 120°. After 2 hours, 30 ml of 1,2-dichloroethane was added and the reaction mixture refluxed for an additional 2 hours. At the end of this time the reaction mixture was distributed between 10% NaOH solution and 2-butanone, after which the organic phase was separated, dried, concentrated and purified by flash chromatography (5% i-PrOH/CH2Cl2). Combination of the product-containing fractions gave 2.61 g of product that was pure to thin layer chromatography. This product was combined with that obtained in another run and recrystallized from EtOAc to give analytically pure material, mp 210°-212°.

後処理

  1. customwas obtained
  2. temperaturethe reaction mixture heated at 120°
  3. temperaturethe reaction mixture refluxed for an additional 2 hours
  4. customafter which the organic phase was separated
  5. customdried
  6. concentrationconcentrated
  7. custompurified by flash chromatography (5% i-PrOH/CH2Cl2)

出典と根拠

ORDレコード
ord-95466a2915a543f5bae252fcc77eb8e9
出典データセット
uspto-grants-1993_05
特許番号
US05208330

関連ノート

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