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

HRID 361401

반응식

HRID 361401 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c2596aef61f547bbb6404bb4e3aa411c
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05866579

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