Hydrochloric Acid → Methyl 2-(phenylamino)acetate

To a stirred solution of the N-phenylglycine (5.45 g, 36 mmol) in methanol (100 mL) was added hydrogen chloride (50 mL, 4.0 M solution in dioxane, 200 mmol) and the mixture was stirred overnight at rt. The organic solvent was removed under reduced pressure and the residue was dissolved in dichloromethane (100 mL), washed with 1N sodium carbonate (3×50 mL), brine (50 mL), dried over Na2SO4, filtered, concentrated under reduced pressure and finally dried in vacuo to afford 5.85 g (98%) of the title compound. 1H NMR (400 MHz, CDCl3) δ: 7.2 (m, 2H), 6.76 (m, 1H), 6.62 (m, 2H), 4.27 (brs, 1H), 3.93 (d, 2H), 3.78 (s, 3H).

1. customThe organic solvent was removed under reduced pressure
2. dissolutionthe residue was dissolved in dichloromethane (100 mL)
3. washwashed with 1N sodium carbonate (3×50 mL), brine (50 mL)
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customfinally dried in vacuo

ORD record

ord-1bc455e845e74c3f8c303cf177197981

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07160902B2