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

HRID 1836288Notes

Reaction equation

HRID 1836288 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 (0.805 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 C12H15N4·1.5C4H4·0.5H2O: 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 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

Sources & evidence

ORD record
ord-a2e51a1f64414b38b518b50fad332546
Source dataset
uspto-grants-2004_08
Patent number
US06777426B2

Reaction notes

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