Benzyl Bromide → HCID 20523224, compound

Participants

Reaction Steps

A mixture of 25.7 grams (115 mmoles) benzyl bromide and 16.7 grams (137 mmoles) 2-hydroxyiminomethyl-pyridine in dimethyl formamide (70 ml) was stored 7 days at room temperature. The precipitate was filtered off and washed with ethanol and ether. Recrystallization from 96% ethanol yielded 30.9 gram (77%) of the compound 1 in the form of white crystals. (a) In case (hetero)arylmethyl chlorides were used instead of bromides or iodides the reaction mixture was heated at 60°-90° C. for 3 to 4 hours. (b) Cyclohexylmethyl iodide alkylated 2-hydroxyiminomethylpyridine with great difficulty. After reaction at 100° C. for 10 hours a product was precipitated with ether. Recrystallisation yielded a mixture of compound 30 and of the hydroiodide of 2-hydroxyiminomethyl-pyridine from which the compound 30 could be recovered by washing with water.

Provenance & Evidence