Hydrochloric Acid → (8-Fluoro-2-phenylquinolin-3-yl)methanamine

HRID 216815Notes

Reaction equation

HRID 216815 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:8]([CH2:18][NH:19]C(=O)C)=[CH:7]2.Cl>>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:8]([CH2:18][NH2:19])=[CH:7]2

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 57708035N-((8-fluoro-2-phenylquinolin-3-yl)methyl)acetamide

Product 1

HCID 57707794(8-Fluoro-2-phenylquinolin-3-yl)methanamine

Procedure

To N-((8-fluoro-2-phenylquinolin-3-yl)methyl)acetamide (28 mg, 95 μmol) was added hydrochloric acid (2 M solution in water, 2 mL, 4000 μmol). The reaction was heated to 80 C for 24 h. The reaction was cooled to rt and quenched with 15% NaOH. The product was extracted into ether (2×10 mL) and the combined organics were washed with brine, dried over MgSO4, filtered, and concentrated to afford (8-fluoro-2-phenylquinolin-3-yl)methanamine. 1H NMR (400 MHz, CDCl3) δ ppm 8.34 (s, 1H), 7.65 (d, J=8.2 Hz, 1H), 7.61 (m, 2H), 7.48 (m, 4H), 7.39 (ddd, J=10.6, 7.8, 1.6 Hz, 1H), 4.05 (s, 2H), 2.03 (br s, 2H). Mass Spectrum (ESI) m/e=253.0 (M+1).

Workup

  1. temperatureThe reaction was heated to 80 C for 24 h
  2. customquenched with 15% NaOH
  3. extractionThe product was extracted into ether (2×10 mL)
  4. washthe combined organics were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bd1563b794494c5e901d753f8893547f
Source dataset
uspto-grants-2012_06
Patent number
US08193199B2

Reaction notes

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