3-Chloroaniline → HCID 31698646, compound

A solution of 6-methylpicolinic acid (5.0 g, 36 mmol) in THF (60.0 ml) was treated with two drops of DMF and 3.5 ml (5.09 g, 40 mmol, 1.1 equiv.) of oxalyl chloride were added dropwise. The solution was stirred for 30 min at room temperature. The reaction mixture was then evaporated to dryness in vaccuo. The residue was taken up in 40 ml of dry THF, and cooled to 0° C. Triethylamine (6.1 ml, 4.43 g, 44 mmol, 1.2 equiv.), and a solution of 4.23 ml (5.12 g, 40 mmol, 1.1 equiv.) of 3-chloro-aniline in 15 ml of dry THF were added dropwise at 0° C. The reaction mixture was stirred for 5 min. at 0° C. and then allowed to warm up to room temperature. After stirring for 1 h at r.t., the dark brown suspension was filtered. The filtrate was concentrated in vaccuo, and the residue was dissolved in 200 ml of ethyl acetate, which was washed once with brine. The aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated in vaccuo. Concentration in vaccuo yielded 7.7 g of a dark brown residue which was purified by flash chromatography (heptane/ethyl acetate 4:1) to yield a the title compound as a white solid (total 5.05 g, 56%), MS (ISP): m/e=247.1, 249.1 (M+H+).

1. additionwere added dropwise
2. customThe reaction mixture was then evaporated to dryness in vaccuo
3. temperaturecooled to 0° C
4. stirringThe reaction mixture was stirred for 5 min. at 0° C.
5. temperatureto warm up to room temperature
6. stirringAfter stirring for 1 h at r.t.
7. filtrationthe dark brown suspension was filtered
8. concentrationThe filtrate was concentrated in vaccuo
9. dissolutionthe residue was dissolved in 200 ml of ethyl acetate
10. washwhich was washed once with brine
11. extractionThe aqueous phase was extracted with ethyl acetate
12. dry with materialThe combined organic phases were dried over magnesium sulfate
13. filtrationfiltered
14. concentrationconcentrated in vaccuo
15. concentrationConcentration in vaccuo

ORD record

ord-721c6d0a68524543ad0e8bb0e773572b

Source dataset

uspto-grants-2008_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07414060B2