Benzenemethanamine, 2-amino-4-fluoro- (9CI) synthesis
- Product Name:Benzenemethanamine, 2-amino-4-fluoro- (9CI)
- CAS Number:733736-89-5
- Molecular formula:C7H9FN2
- Molecular Weight:140.1582
119023-25-5
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Yield:733736-89-5 61%
Reaction Conditions:
Stage #1: 4-fluoroanthranilamidewith dimethylsulfide borane complex in tetrahydrofuran; for 9 h;Heating / reflux;
Stage #2: with water in tetrahydrofuran;
Steps:
3.3
Stage 3: 2-aminomethyl-5-fluorophenylamine 2 M borane-dimethyl sulfide complex (40 ml, 80 mmol) in tetrahydrofuran was added to a solution of the product from stage 2 (2.45 g, 16 mmol) in anhydrous tetrahydrofuran (50 ml) and the mixture was heated under reflux for 9 hours. Water (4 ml) was cautiously added to the cooled reaction solution and the mixture was then concentrated in vacuo. Toluene (2*) was added to the residue and the mixture was concentrated again each time. The residue was then repeatedly dissolved in methanol (3*) and concentrated each time. The crude product was purified by flash chromatography with chloroform/methanol (7:3) and 1% triethylamine. Yield: 1.37 g (61%), white solid. Melting point: 49-51° C.
References:
US2008/293749,2008,A1 Location in patent:Page/Page column 13
940054-57-9
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446-32-2
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