Anthranilic Acid → 2-Amino-N,N-dimethylbenzamide

Temperature

0 °C

A solution of 2-aminobenzoic acid (1.0 g, 7.3 mmol) in thionyl chloride (20 mL) was refluxed for 3 hours. Excess of thionyl chloride was removed. And the residue was treated with toluene (3×10 mL) to remove the excess thionyl chloride. To the crude product obtained was added THF (20 mL) and the resulting solution was cooled to 0° C. Diethyl amine (3.78 mL, 36 mmol) was added and the resulting solution was stirred for 2 hrs at room temperature. The solvent was removed under reduced pressure and residue was taken into dichloromethane (20 mL), washed with saturated sodium bicarbonate solution (3×20 mL), water (20 mL), dried over sodium sulfate and concentrated to provide the desired product as brown oil. This crude product was used in Step 2 without further purification.

1. customExcess of thionyl chloride was removed
2. additionAnd the residue was treated with toluene (3×10 mL)
3. customto remove the excess thionyl chloride
4. customTo the crude product obtained
5. customThe solvent was removed under reduced pressure and residue
6. washwashed with saturated sodium bicarbonate solution (3×20 mL), water (20 mL)
7. dry with materialdried over sodium sulfate
8. concentrationconcentrated

ORD record

ord-fb3cdf3433bc4f24b26a54e9d9d2da13

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08349827B2