Sodium Hydroxide → 5,6-Dihydro-8-methoxy-2-(quinolin-2-ylmethylthio)-4H-imidazo-[4,5,1-ij]quinoline

HRID 256308ノート

反応式

HRID 256308 の反応式
Cl.Cl[CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:23]3=[C:24]([NH:26][C:27](=[S:28])[N:22]3[CH2:21][CH2:20][CH2:19]2)[CH:25]=1.[OH-].[Na+]>CCO>[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:23]3=[C:24]([N:26]=[C:27]([S:28][CH2:3][C:4]4[CH:13]=[CH:12][C:11]5[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=5)[N:5]=4)[N:22]3[CH2:21][CH2:20][CH2:19]2)[CH:25]=1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 30838232-(Chloromethyl)quinoline hydrochlorideHCID 135032135,6-dihydro-8-methoxy-2-mercapto-4H-imidazo[4,5,1-ij]quinoline

生成物 1

HCID 135032105,6-Dihydro-8-methoxy-2-(quinolin-2-ylmethylthio)-4H-imidazo-[4,5,1-ij]quinoline収率 62%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

2-Chloromethylquinoline hydrochloride (0.845 g, 4.0 mmol) was added to a solution of 5,6-dihydro-8-methoxy-4H-imidazo[4,5,1-ij]quinoline-2(1H)-thione (0.871 g, 4.0 mmol) in 1 N-NaOH (8 ml) and EtOH (8 ml). The mixture was heated to reflux, cooled to room temperature, concentrated in vacuo, and the aqueous residue extracted with CH2Cl2 (50 ml). The extract was washed with 1NNaOH (2×30 ml), and brine (20 ml), dried (MgSO4), and evaporated in vacuo to give an oil which was purified by chromatography (SiO2, Et2O) and trituration with Et2O-petrol ether to give the title compound (0.885 g, 62%) as yellow crystals, mp 89°-91° C. (Found: C,70.1; H,5.4; N,11.4; C21H19N3OS requires C,69.8; H,5.3; N,11.6%).

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. concentrationconcentrated in vacuo
  4. extractionthe aqueous residue extracted with CH2Cl2 (50 ml)
  5. washThe extract was washed with 1NNaOH (2×30 ml), and brine (20 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated in vacuo
  8. customto give an oil which
  9. customwas purified by chromatography (SiO2, Et2O) and trituration with Et2O-petrol ether

出典と根拠

ORDレコード
ord-8e855320f1a2430bbb493ebb67084ef2
出典データセット
uspto-grants-1987_10
特許番号
US04703044

反応ノート

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