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

HRID 2289513Notes

Reaction equation

HRID 2289513 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of the above solid (0.221 g, 1.49 mmole), 2-imidazoline-2-sulfonic acid (0.005 g, 5.4 mmole) and isobutyl alcohol (4 mL) was refluxed for 18 hours. The solveunt 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.

Workup

  1. temperaturewas refluxed for 18 hours
  2. customThe solveunt 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

Sources & evidence

ORD record
ord-7d7daf6b1edb4d009193613e5200cb1d
Source dataset
uspto-grants-2000_07
Patent number
US06093727

Reaction notes

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