Hydrazine hydrate (1:1) → 4-(4-Aminobutyryl)-8-chloro-1,2,3,4,5,6-hexahydrobenzo[f]quinoline hydrochloride
Reaction equation
[Cl:1][C:2]1[CH:31]=[CH:30][C:5]2[C:6]3[CH2:7][CH2:8][CH2:9][N:10]([C:14](=[O:29])[CH2:15][CH2:16][CH2:17][N:18]4C(=O)C5=CC=CC=C5C4=O)[C:11]=3[CH2:12][CH2:13][C:4]=2[CH:3]=1.O.NN>C(O)C>[ClH:1].[NH2:18][CH2:17][CH2:16][CH2:15][C:14]([N:10]1[C:11]2[CH2:12][CH2:13][C:4]3[CH:3]=[C:2]([Cl:1])[CH:31]=[CH:30][C:5]=3[C:6]=2[CH2:7][CH2:8][CH2:9]1)=[O:29]Participants
4
Procedure
A suspension of 10.9 g (0.025 mol) of 8-chloro -1,2,3,4,5,6-hexahydro-4-(4-phthalimidobutyryl)benzo[f]-quinoline and 3.2 ml (0.065 mol) of hydrazine hydrate in 150 ml of ethanol is boiled at reflux temperature for 2 hours. The solution is concentrated, extracted with methylene chloride/water dried with sodium sulfate and the solvent is distilled in a vacuum. The residue is dissolved in 10 ml of 5.5N methanolic hydrochloric acid and precipitated with ether. Recrystallization from methanol/ether gives 4-(4-aminobutyryl)-8-chloro -1,2,3,4,5,6-hexahydrobenzo[f]quinoline hydrochloride as beige crystals with melting point 225°.
Workup
- temperatureat reflux temperature for 2 hours
- concentrationThe solution is concentrated
- extractionextracted with methylene chloride/water
- dry with materialdried with sodium sulfate
- distillationthe solvent is distilled in a vacuum
- dissolutionThe residue is dissolved in 10 ml of 5.5N methanolic hydrochloric acid
- customprecipitated with ether
- customRecrystallization from methanol/ether
Sources & evidence
- ORD record
- ord-a9d09531c6384200a73226e39be8e798
- Source dataset
- uspto-grants-1991_05
- Patent number
- US05017608
Reaction notes
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