Pyridine → Methyl 2-[(methylsulfonyl)amino]benzoate

Methanesulfonyl chloride (3.4 mL, 44 mmol) was added to a solution of methyl anthranilate (5.0 mL, 39 mmol) in pyridine (10 mL, 124 mmol). Mixture stirred at room temperature for 16 hours. Reaction was quenched with 1N hydrochloric acid (150 mL). Mixture was extracted with ethyl acetate (2×200 mL). Organic layers were washed successively with 1N hydrochloric acid (2×100 mL) and brine (50 mL). Organic layer was dried (magnesium sulfate), filtered and concentrated in vacuo. Residue was crystallized from 50 mL isopropyl alcohol. Solids were filtered, washed with isopropyl alcohol and dried in vacuo. Title compound was obtained as pink crystals in 75% yield. MS m/e (M−H)−=228.0.

1. customReaction
2. customwas quenched with 1N hydrochloric acid (150 mL)
3. extractionMixture was extracted with ethyl acetate (2×200 mL)
4. washOrganic layers were washed successively with 1N hydrochloric acid (2×100 mL) and brine (50 mL)
5. dry with materialOrganic layer was dried (magnesium sulfate)
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customResidue was crystallized from 50 mL isopropyl alcohol
9. filtrationSolids were filtered
10. washwashed with isopropyl alcohol
11. customdried in vacuo

ORD record

ord-e54c1efd894f49a993178bb5fd10b648

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07544680B2