Sodium Hydroxide → HCID 68718322, compound

Participants

Reaction Conditions

Reaction Steps

N-[(E)-1-Acetyl-2-aminoethenyl]-N-isopropylpropanamide (Method 7; 373 g, 1.0 eq.) was stirred with sodium hydroxide (1.4 eq.) in EtOH (4 vol.eq.). The reaction was heated to reflux (85° C.) and stirred overnight. Ammonium chloride (2.0 eq.) was then added and this was stirred for 2 hours (the consistency of the reaction changed to a fine precipitate). The reaction was then allowed to cool, the solid was filtered off and discarded, and the solvent was then removed in vacuo. Acetone was then added to the residue, the solid was filtered off and discarded. The solvent was then removed in vacuo. Prep chromatography was then performed by eluting with 5% MeOH/DCM, to leave a brown oil (290 g, 86%). NMR 1.23 (3H, t), 1.43 (6H, d), 2.40 (3H, s), 2.77 (2H, q), 5.0 (1H, b s), 7.87 (1H, s).

Provenance & Evidence