Reaction #543542

Reaction equation

12-phthalimido-3,3,9,9-tetramethyl-5-oxa-4,8-diaza-2,10-dodecane dione dioxime

12-Phthalimido-3,3,9,9-tetramethyl-5-oxa-4,8-diaza-2,10-dodecanedione dioxime

hydrazine

→

12-Amino-3,3,9,9-tetramethyl-5-oxa-4,8-diaza-2,10-dodecanedione dioxime

Solvents

methylene chloride

Conditions

Workup

1. 1
   Temperaturethe reaction mixture was refluxed for 3 h
2. 2
   OtherThe white solid formed
3. 3
   Filtrationwas filtered
4. 4
   Washthe filter cake was washed with methylene chloride (50 mL)
5. 5
   ConcentrationThe combined filtrate and the washings were concentrated
6. 6
   Otherto give a thick oil which
7. 7
   Otherwas dried under vacuum
8. 8
   Otherto afford a white solid
9. 9
   OtherThis was used in the next step without further purification

Procedure

To a solution of 12-phthalimido-3,3,9,9-tetramethyl-5-oxa-4,8-diaza-2,10-dodecane dione dioxime (52a) (2.0 g, 4.6 mmol) in methylene chloride (100 mL) was added hydrazine (0.3 mL, 9.3 mmol) and the reaction mixture was refluxed for 3 h. The white solid formed was filtered and the filter cake was washed with methylene chloride (50 mL). The combined filtrate and the washings were concentrated to give a thick oil which was dried under vacuum to afford a white solid. Yield: 1.2 g (82%). MS: (M+H)+=304.1. This was used in the next step without further purification.

Source