Formaldehyde → Methyl 2-dimethylamino-3-benzoylphenylacetate

Participants

Reaction Steps

A stirred solution of 4.6 gms. (0.0165 mole) of methyl 2-amino-3-benzoylphenylacetate and 13.2 ml. (0.165 mole) of 37% formaldehyde in 66 ml. of acetonitrile was treated with 3.14 gms. (0.0495 mole) of sodium cyanoborohydride. Glacial acetic acid (1.65 ml.) was added over a ten minute period and stirring contained for 2.0 hrs. at room temperature. An additional 1.65 ml. of glacial acetic acid was added and the mixture stirred over a weekend (co. 65 hours). The mixture was diluted with ether and the ether solution was successively washed with 3 N potassium solution, water, dried over sodium sulfate and concentrated under vacuum to give approximately 1.0 gm. (18%) of a yellow oil. A portion of the oil was molecularly distilled for an analytical sample.

Provenance & Evidence