L-Proline → HCID 68699150, compound

Participants

Reaction Steps

Heat a slurry of 2-chloro-4-fluoro-3-methyl-benzonitrile (0.4 g, 2.36 mmol) and L-proline (2.11 g, 18.8 mmol) in N-methylmorpholine (1.6 mL) at 200° C. in a microwave for 30 min. Partition the reaction between 2N aqueous hydrochloric acid and ethyl acetate. Separate and extract the organic portion with 2N aqueous sodium hydroxide. Acidify the aqueous extract to pH 1 by adding concentrated hydrochloric acid and back extract into ethyl acetate. Extract the combined organic portions with brine, dry over magnesium sulphate, filter, and concentrate under reduced pressure to give the title compound. (0.395 g, 63%) mass spectrum (m/e): 263 (M−1); 1H NMR (300 MHz, CDCl3): δ 8.66 (bs, 1H0, 7.31 (d, 1H), 6.75 (d, 1H), 4.38 (t, 1H), 3.67 (m, 1H), 3.10 (m, 1H), 2.43 (m, 1H), 2.29 (s, 3H), 2.20-1.90 (m. 3H).

Provenance & Evidence