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

HRID 256307ノート

反応式

HRID 256307 の反応式
[NH:1]1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][N:3]3[C:2]1=[S:13].[OH-].[Na+].Cl.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)C>[N:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:27]=[CH:28][C:19]=1[CH2:18][S:13][C:2]1[N:3]2[C:12]3[C:7]([CH2:6][CH2:5][CH2:4]2)=[CH:8][CH:9]=[CH:10][C:11]=3[N:1]=1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 30838232-(Chloromethyl)quinoline hydrochlorideHCID 134578575,6-dihydro-2-mercapto[4H]imidazo [4,5,1-ij]quinoline

生成物 1

HCID 135032085,6-dihydro-2-(quinolin-2-ylmethylthio)-4H-imidazo[4,5,1-ij]quinoline収率 55.4%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of 5,6-dihydro-4H-imidazo[4,5,1-ij]-quinoline-2(1H)-thione (2.02 g, 11.6 mmol) in ethanol (25 ml) and 1N-sodium hydroxide was treated with 2-(chloromethyl)quinoline hydrochloride (2.48 g, 11.6 mmol) heated to reflux, cooled to room temperature, and the ethanol removed by evaporation in vacuo. The aqueous mixture was filtered and the precipitate washed with water (5×50 ml), dried in vacuo, and recrystallised from cyclohexane - EtOAc to give 5,6-dihydro-2-(quinolin-2-ylmethylthio)-4H-imidazo[4,5,1-ij]quinoline (2.13 g, 55%) as yellow crystals mp 125°-126° C. (Found: C, 72.8; H, 5.3; N,12.4 C20H17N3S requires C, 72.5; H, 5.2; N, 12.7%).

後処理

  1. temperatureheated
  2. temperatureto reflux
  3. customthe ethanol removed by evaporation in vacuo
  4. filtrationThe aqueous mixture was filtered
  5. washthe precipitate washed with water (5×50 ml)
  6. customdried in vacuo
  7. customrecrystallised from cyclohexane - EtOAc

出典と根拠

ORDレコード
ord-d6f32f06ec2046bc8777a1bb1141b6b5
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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