Ammonium Chloride → HCID 86694707, compound

Temperature

80 °C

A mixture of 1-(6-fluoro-1H-benzo[d]imidazol-4-yl)ethanone oxime (351 mg, 1.82 mmol), Zn powder (1.18 g, 18.2 mmol), and NH4Cl (973 mg, 18.2 mmol) in MeOH (50 mL) and HOAc (10 mL) was heated at 80° C. for 4 h. The reaction mixture was filtered and the filtrate concentrated in vacuo. To the residue was added NH4OH (50 mL), and the mixture was extracted with DCM (50 mL×3). The combined extracts were dried (MgSO4), filtered, and concentrated in vacuo. The crude mixture was purified by SiO2 chromatography eluting with DCM/MeOH/TEA (10:1:0.2) to afford 1-(6-fluoro-1H-benzo[d]imidazol-4-yl)ethanamine (121) as a yellow solid (318 mg, 97.7%). MS (ESI): m/z=180.1 [M+1]+.

1. filtrationThe reaction mixture was filtered
2. concentrationthe filtrate concentrated in vacuo
3. additionTo the residue was added NH4OH (50 mL)
4. extractionthe mixture was extracted with DCM (50 mL×3)
5. dry with materialThe combined extracts were dried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe crude mixture was purified by SiO2 chromatography
9. washeluting with DCM/MeOH/TEA (10:1:0.2)

ORD record

ord-16785498efb446e7b487ed404d441751

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08637537B2