Hydrochloric Acid → 1-(3,5-Dimethylanilino)-4-[(pyridin-4-yl)-methyl]-isoquinoline

HRID 396213ノート

反応式

HRID 396213 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([CH3:9])[CH:8]=1)[NH2:5].Cl.Cl[C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH2:22][C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)=[CH:14][N:13]=1>C(O)C>[CH3:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([CH3:9])[CH:8]=1)[NH:5][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH2:22][C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)=[CH:14][N:13]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 79493,5-DimethylanilineHCID 111611391-Chloro-4-(pyridin-4-ylmethyl)-isoquinoline

生成物 1

HCID 98627391-(3,5-Dimethylanilino)-4-[(pyridin-4-yl)-methyl]-isoquinoline

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
90 °C

実験手順

With the exclusion of moisture, 100 mg (0.825 mmol) of 3,5-dimethyl-aniline are dissolved in 4 ml of ethanol, and 196 μl (0.784 mmol) of HCl (4N in dioxane) are added. After the addition of 200 mg (0.785 mmol) of 1-chloro-4-[(pyridin-4-yl)-methyl]-isoquinoline, the mixture is heated for 8 hours at 90° C. Concentration by evaporation is then carried out; the residue is taken up in 4 ml of water, 1 ml of saturated ammonia solution and 20 ml of CH2Cl2, and the organic phase is separated off, dried with Na2SO4 (anhydrous) and concentrated by evaporation again. Column chromatography (SiO2; ethyl acetatelhexane 3:1) and crystallisation from ethyl acetate/hexane yield the title compound: m.p. 156-158° C.; 1H NMR (DMSO-d6) 9.00 (s, HN), 8.54 (d, 1H), 8.42 (d, 2H), 8.00 (s, 1H), 7.80 (d, 1H), 7.65 (m, 2H), 7.50 (s, 2H), 7.26 (d, 2H), 6.64 (s, 1H), 4.25 (s, 2H), 2.27 (s, 6H); FAB-MS: (M+H)+=340; Anal. calc. (C23H21N3.0.1H2O) C 80.95%, H 6.26%, N 12.31%; found C 80.9%, H 6.2%, N 12.4%.

後処理

  1. concentrationConcentration
  2. customby evaporation
  3. custom1 ml of saturated ammonia solution and 20 ml of CH2Cl2, and the organic phase is separated off
  4. dry with materialdried with Na2SO4 (anhydrous)
  5. concentrationconcentrated by evaporation again
  6. customColumn chromatography (SiO2; ethyl acetatelhexane 3:1) and crystallisation from ethyl acetate/hexane

出典と根拠

ORDレコード
ord-82755828494e44848017c4522911c709
出典データセット
uspto-grants-2003_08
特許番号
US06608071B2

反応ノート

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