2-(dimethylaminomethylidene)cyclopentane-1,3-dione

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1.3 grams of benzylhydrazine dihydrochloride and 2.8 ml of 5 N sodium hydroxide in 10 ml of methanol was added to an ice-cold solution of 2-dimethylaminomethylene-1,3-cyclopentanedione in 20 ml of methanol. The mixture was heated at reflux for 2 hours and concentrated under reduced pressure. The residue was extracted several times with dichloromethane and the combined dichloromethane extracts were dried over magnesium sulfate and concentrated under reduced pressure to give a fluffy yellow solid. This was recrystallized from a mixture of toluene and hexane to give 2-[(2-benzylhydrazino)methylene]-1,3-cyclopentanedione melting about 164° C. with decomposition. The mixture was heated at reflux for 2 hours concentrated under reduced pressure The residue was extracted several times with dichloromethane the combined dichloromethane extracts were dried over magnesium sulfate concentrated under reduced pressure to give a fluffy yellow solid This was recrystallized from a mixture of toluene and hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1.3 grams of benzylhydrazine dihydrochloride and 2.8 ml of 5 N sodium hydroxide in 10 ml of methanol was added to an ice-cold solution of 2-dimethylaminomethylene-1,3-cyclopentanedione in 20 ml of methanol. The mixture was heated at reflux for 2 hours and concentrated under reduced pressure. The residue was extracted several times with dichloromethane and the combined dichloromethane extracts were dried over magnesium sulfate and concentrated under reduced pressure to give a fluffy yellow solid. This was recrystallized from a mixture of toluene and hexane to give 2-[(2-benzylhydrazino)methylene]-1,3-cyclopentanedione melting about 164° C. with decomposition. The mixture was heated at reflux for 2 hours concentrated under reduced pressure The residue was extracted several times with dichloromethane the combined dichloromethane extracts were dried over magnesium sulfate concentrated under reduced pressure to give a fluffy yellow solid This was recrystallized from a mixture of toluene and hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1.3 grams of benzylhydrazine dihydrochloride and 2.8 ml of 5 N sodium hydroxide in 10 ml of methanol was added to an ice-cold solution of 2-dimethylaminomethylene-1,3-cyclopentanedione in 20 ml of methanol. The mixture was heated at reflux for 2 hours and concentrated under reduced pressure. The residue was extracted several times with dichloromethane and the combined dichloromethane extracts were dried over magnesium sulfate and concentrated under reduced pressure to give a fluffy yellow solid. This was recrystallized from a mixture of toluene and hexane to give 2-[(2-benzylhydrazino)methylene]-1,3-cyclopentanedione melting about 164° C. with decomposition. The mixture was heated at reflux for 2 hours concentrated under reduced pressure The residue was extracted several times with dichloromethane the combined dichloromethane extracts were dried over magnesium sulfate concentrated under reduced pressure to give a fluffy yellow solid This was recrystallized from a mixture of toluene and hexane