Hydrazine hydrate (1:1) → 7-Aminohept-5-ynoic Acid
Reaction equation
O.NN.C1(=O)[N:8]([CH2:9][C:10]#[C:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])C(=O)C2=CC=CC=C12>C(O)C>[NH2:8][CH2:9][C:10]#[C:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
Hydrazine hydrate (0.1 ml) was added to a solution of 7-phthalimidohept-5-ynoic acid (0.55 g) in ethanol (25 ml). The mixture was refluxed for 3.5 hours and then the solvent was removed under reduced pressure. The residue was suspended in water (20 ml), the pH of the solution was adjusted to 5, and the solid was collected by filtration. The filtrate was evaporated to dryness and the residue was extracted with ethanol (3×5 ml). The ethanol extracts were cooled (5° C.) and the resulting precipitate was collected to give the title compound (0.19 g) m.p. 180°-183° C.
Workup
- temperatureThe mixture was refluxed for 3.5 hours
- customthe solvent was removed under reduced pressure
- filtrationthe solid was collected by filtration
- customThe filtrate was evaporated to dryness
- extractionthe residue was extracted with ethanol (3×5 ml)
- customthe resulting precipitate was collected
Sources & evidence
- ORD record
- ord-f3efc93560af4e3485c6e2496ad49052
- Source dataset
- uspto-grants-1991_03
- Patent number
- US04997847
Reaction notes
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