Isobutanol → 2-(5,6,7,8-Tetrahydroquinolin-3-yl)amino-2-imidazoline

HRID 361401ノート

反応式

HRID 361401 の反応式
[NH:1]1[CH2:5][CH2:4][N:3]=[C:2]1S(O)(=O)=O.[CH2:10](O)[CH:11]([CH3:13])[CH3:12].[C:15](O)(=O)/[CH:16]=[CH:17]/C(O)=O>C(O)C>[N:1]1[C:12]2[CH2:15][CH2:16][CH2:17][CH2:13][C:11]=2[CH:10]=[C:4]([NH:3][C:2]2[NH:1][CH2:5][CH2:4][N:3]=2)[CH:5]=1

参加物

5

反応物 3

HCID 6560IsobutanolHCID 2745614,5-dihydro-1H-imidazole-2-sulfonic acidHCID 444972Fumaric Acid

生成物 1

HCID 234991692-(5,6,7,8-Tetrahydroquinolin-3-yl)amino-2-imidazoline収率 59%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of the above solid (0.221 g, 1.49 mmole), 2-imidazoline-2-sulfonic acid (0.805 g, 5.4 mmole) and isobutyl alcohol (4 mL) was refluxed for 18 hours. The solvent was removed in vacuo and the residue was flash chromatographed over silica gel (eluent: 10:2:1 v/v/v ethyl acetate-methanol-triethylamine). The product was obtained in 100% yield (0.337 g) as a pale yellow solid. The above solid was treated in ethanol with 1.0 equivalent of fumaric acid to give a fumarate as a white solid (59% yield): mp 201°-203° C. Anal. Calcd. for C12H16N4.1.5C4H4O4.0.5H2O: C, 54.13; H, 5.76; N, 14.04. Found: C, 54.04; H, 5.96; N, 13.69.

後処理

  1. temperaturewas refluxed for 18 hours
  2. customThe solvent was removed in vacuo
  3. customchromatographed over silica gel (eluent: 10:2:1 v/v/v ethyl acetate-methanol-triethylamine)
  4. customThe product was obtained in 100% yield (0.337 g) as a pale yellow solid

出典と根拠

ORDレコード
ord-c2596aef61f547bbb6404bb4e3aa411c
出典データセット
uspto-grants-1999_02
特許番号
US05866579

反応ノート

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