Hydrochloric Acid → [4-(4,5-Dihydro-1H-imidazol-2-yl)phenyl]acetic acid

To a solution of (4-cyanophenyl)acetic acid (131 mg, 0.816 mmol) in EtOH (0.5 mL) at 0° C. was bubbled HCl(g) until saturation. Reaction mixture was allowed to warm to room temperature slowly. After overnight stirring, the crude reaction mixture was concentrated in vacuo. This residue was taken up in EtOH (4 mL) and ethylene diamine (0.1 mL, 1.49 mmol) was added. After stirring at room temperature for two hours, the crude reaction mixture was concentrated under reduced pressure and then re-dissolved in DMF (2 mL). To this solution was added 1M NaOH (2 mL, 2 mmol) and the reaction stirred at room temperature for three hours. Crude reaction mixture was neutralized with 1M HCl to a pH 6 and extracted with CHCl3 (4×15 mL). Product was found in the water layer, so combined all layers and concentrated in vacuo, re-dissolved in CHCl3/MeOH, and filtered to remove precipitate. Concentration of the filtrate gives [4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]acetic acid, which was used without further purification. LCMS (ES) 205.1 m/z (M+H)+

1. customReaction mixture
2. customthe crude reaction mixture
3. concentrationwas concentrated in vacuo
4. stirringAfter stirring at room temperature for two hours
5. customthe crude reaction mixture
6. concentrationwas concentrated under reduced pressure
7. dissolutionre-dissolved in DMF (2 mL)
8. stirringthe reaction stirred at room temperature for three hours
9. customCrude reaction mixture
10. extractionextracted with CHCl3 (4×15 mL)
11. concentrationconcentrated in vacuo
12. dissolutionre-dissolved in CHCl3/MeOH
13. filtrationfiltered
14. customto remove precipitate

ORD record

ord-5aa0976e8bc44598a08a3afa6f67dd11

Source dataset

uspto-grants-2005_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06908921B2