Sodium Carbonate → HCID 20309480, compound

Participants

Reaction Steps

Hydrazine hydrate (1.57 ml, 0.0314 mole) was added to a stirred solution of ethyl 3-[2-(3-t-butylamino-2-hydroxypropoxy)-4-chlorobenzoyl]propionate (2.4 g, 0.0065 mole) in glacial acetic acid (36 ml) and the solution was heated under reflux for 90 minutes. Evaporation under reduced pressure gave an oil which was dissolved in water, treated with an excess of aqueous sodium carbonate solution and the mixture was extracted with dichloromethane. Evaporation of the dried or ganic extracts gave an oil which was purified on a silica column by elution with mixtures of chloroform and methanol to give 6-[2-(3-t-butylamino-2-hydroxypropoxy)-4-chlorophenyl]-4,5-dihydro-3(2H)-pyridazinone (1.1 g, 50%, m.p. (195° ). The hemisulphate, crystallised from ethanol, had m.p. 250° (decomposition). (Found: C, 50.19; H, 6.21; Cl, 8.75; N, 10.11; S, 3.89; M+, 353/355. C17H24ClN3O3.0.53 H2SO 4 requires; C, 50.31; H. 5.96; Cl, 8.74; N, 10.35; S, 4.17%; M(base), 353/355).

Provenance & Evidence