Sulfuric Acid → 6-Chloropyridine-3-carbaldehyde

Temperature

0 °C

Combine 6-chloro-nicotino-nitrile (1.00 g, 7.21 mmol) and toluene (24 mL). Cool the resulting solution at 0° C. and add DIBAL-H (1.0 M in toluene, 7.58 mL, 7.58 mmol) dropwise. Stir the resulting red solution at 0° C. for 1 h. Then, add methanol (2 mL) followed by H2SO4 (aq. 2.0 M, 6 mL). Stir for 1 h at rt. Add CHCl3:isopropanol (3/1, 15 mL) and wash with Rochelle's salt solution (20 mL), followed by NaHCO3 (20 mL) and brine. Dry the combined organic layers over magnesium sulfate, filter and concentrate. Purify by flash chromatography (EtOAc/hexanes 10%) to give the title compound (530 mg, 62%).

1. stirringStir for 1 h at rt
2. washAdd CHCl3:isopropanol (3/1, 15 mL) and wash with Rochelle's salt solution (20 mL)
3. dry with materialDry the combined organic layers over magnesium sulfate
4. filtrationfilter
5. concentrationconcentrate
6. customPurify by flash chromatography (EtOAc/hexanes 10%)

ORD record

ord-11f65d50ccb94616be56241ee9ec4429

Source dataset

uspto-grants-2008_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07381719B2