5-AMino-2-fluoro-benzeneacetic acid Methyl ester HCl synthesis

Yield:1338367-30-8 89%

Reaction Conditions:

with palladium 10% on activated carbon;hydrogen in methanol at 20; for 76 h;

Steps:

1a.2 methyl 2-(5-amino-2-fl uorophenyl)acetate

Step 2: methyl 2-(2-fluoro-5-nitrophenyl)acetate Ex.4a (10.6 g, 49.7 mmol) was dissolved in MeOH (200 mL). The mixture was purged with nitrogen. A catalytic amount of Pd/C (10%) was added under nitrogen atmosphere. The nitrogen atmosphere was replaced by hydrogen and the mixture was stirred for 1 6h at rt. Hydrogenation was continued for 60h. The mixture was filtered through a pad of Celite and washed with MeOH. The filtrate was concentrated to dryness to afford a yellow oil. The crude material was purified by column chromatography eluting with heptane and a gradient of heptane/EtOAc from [100:0] to [70:30]. The product fractions were combined and concentrated to dryness to afford methyl 2-(5-amino-2-fluorophenyl)acetate Ex.4b (8.11 g, 89%) as pale brown oil.

References:

WO2018/138359,2018,A1 Location in patent:Page/Page column 41; 42; 43