3-Chlorobenzaldehyde → HCID 74762708, compound

Participants

Reaction Steps

5-bromo-4-methylpyridin-2-amine (200 mg, 1.07 mmol, Eq: 1.00), 3-chlorobenzaldehyde (158 mg, 128 μl, 1.12 mmol, Eq: 1.05) and p-toluenesulfonic acid monohydrate (61.0 mg, 321 μmol, Eq: 0.3) were dissolved in MeOH (1.5 mL) and the intensive yellow solution was stirred for 5 min. To this yellow solution was added dropwise 2-isocyano-2-methylpropane (88.9 mg, 122 μL, 1.07 mmol, Eq: 1.00) and the corresponding yellow solution was stirred for 3 h. To the reaction solution was added water dropwise, leading to a milky suspension (product oiled out). The water/MeOH phase was removed and the oily residue was treated with MeOH (1 mL) and dropwise addition of water. Again a milky suspension was formed and the product oiled out. Upon standing for an hour crystals formed from the oily phase. The crystals were filtered off and washed with water and MeOH, dried under high vacuum to yield the product (148 mg, 35.2%). MS: 394.1 [M+H]+; 1H-NMR (D6-DMSO): δ 8.62 (s, 1H), 8.27 (s, 1H), 8.16 (d, 1H), 7.51 (s, 1H), 7.44 (t, 1H), 7.34 (d, 1H), 4.77 (s, 1H), 2.40 (s, 3H), 1.03 (s, 9H).

Provenance & Evidence