ChemicalBook CAS DataBase List 4-FLUORO-N-METHYLBENZAMIDE

4-FLUORO-N-METHYLBENZAMIDE synthesis

11synthesis methods

Product Name:4-FLUORO-N-METHYLBENZAMIDE
CAS Number:701-49-5
Molecular formula:C8H8FNO
Molecular Weight:153.15

456-22-4 Synthesis

456-22-4
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$10.00/100 g

74-89-5 Synthesis

74-89-5
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$13.44/25ML

701-49-5
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$10.00/250mg

Yield:701-49-5 63%

Reaction Conditions:

Stage #1:4-Fluorobenzoic acid;methylamine with triethylamine in tetrahydrofuran;1,2-dichloro-ethane at 20; for 0.166667 h;
Stage #2: with benzotriazol-1-ol;dicyclohexyl-carbodiimide in tetrahydrofuran;1,2-dichloro-ethane at 70; for 3 h;

Steps:

4.D; D
To a stirred solution of 4-fluorobenzoic acid (200 mg, 1.43 mmol) in DCE (3 ml) at RT, was added a solution of methyl amine in THF (2 M, 1.43mmol) and NEt₃ (198 μl, 1.43 mmol) and allowed to stir for ca. 10 mins. HOBt (221 mg, 1.43 mmol) and DCC (295 mg, 1.43 mmol) were added and the reaction mixture heated at 70 ⁰C for 3 h. After cooling to RT, the reaction mixture was washed with sat. NaHCO₃ (5 ml) and the aqueous back extracted with DCM. The organics were combined, dried (MgSO₄), filtered and concentrated under reduced pressure. Purification by silica flash column chromatography (eluting with DCM/MeOH gradient 100:0 to 80:20) provided the title compound as off-white solid (137 mg, 63%).LCMS data: Calculated MH⁺ (154); Found 100% (MH⁺) m/z 154.2, Rt = 1.11 min.

References:

EVOTEC NEUROSCIENCES GMBH WO2009/135842, 2009, A1 Location in patent:Page/Page column 67-68

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