Pyridine → Methyl 3-(methanesulfonylamino)phenylacetate

HRID 491537Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[CH3:19][S:20](Cl)(=[O:22])=[O:21].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:19][S:20]([NH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:6][CH:7]=1)(=[O:22])=[O:21]

Participants

Conditions

Temperature: 0 °C

Procedure

Methyl 3-aminophenylacetate (2.26 g, 13.7 mmol) was dissolved in dry methylene chloride (20 mL) and cooled to 0° C. Pyridine (2.2 mL, 27.2 mmol) was added followed by dropwise addition of methanesulfonyl chloride (1.3 mL, 16.8 mmol). The mixture was stirred at 0° C. for 1 hour and at room temperature for 3 hours, then poured into 100 mL of saturated sodium bicarbonate solution. The organic layer was washed with saturated sodium bicarbonate (100 mL), 1N HCl (2×100 mL) and brine. Dried over MgSO4. Solvent was evaporated to afford methyl 3-(methanesulfonylamino)phenylacetate. (3.36 g, 100%). 1H NMR (CDCl3) δ 7.32 (1H, dd), 7.2-7.1 (3H, m), 6.57 (1H, s), 3.72 (3H, s), 3.64 (2H, s), 3.02 (3H, s).

Workup

washThe organic layer was washed with saturated sodium bicarbonate (100 mL), 1N HCl (2×100 mL) and brine
dry with materialDried over MgSO4
customSolvent was evaporated

Sources & evidence

ORD record: ord-743fe47789264792abb4b70f367e617d
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07531556B2

Reaction notes

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