Ethyl Acetate → 6-Chloro-N2-methylpyridine-2,3-diamine

To a solution of 6-chloro-N-methyl-3-nitropyridin-2-amine (630 mg, 3.36 mmol) in MeOH (10 ml) and water (10 ml) was added Fe (940.8 mg, 16.8 mmol) and NH4Cl (898.8 mg, 168 mmol) at 20° C. The mixture was stirred for 3 hours under reflux temperature until TLC (PE:EA=3:1) showed that the reaction was complete. The mixture was filtered, the filtrate concentrated and residue treated with water (10 ml) and extracted with ethyl acetate (2×20 ml). The combined organic layers were washed with brine (30 ml), dried over Na2SO4 and concentrated to give the desired product (316 mg, 59.7%) as a yellow solid which was used in next step without further purification. LCMS (m/z): 158.1 [M+H]+.

1. filtrationThe mixture was filtered
2. concentrationthe filtrate concentrated
3. additionresidue treated with water (10 ml)
4. extractionextracted with ethyl acetate (2×20 ml)
5. washThe combined organic layers were washed with brine (30 ml)
6. dry with materialdried over Na2SO4
7. concentrationconcentrated

ORD record

ord-cdeddcd30b9f4b179902be93f9839364

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08906900B2