Hydrochloric Acid → HCID 20485595, compound
Reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[N:18]([O-])=O.[Na+].[ClH:22]>O>[ClH:22].[ClH:22].[NH:1]([C:2]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1)[NH2:18]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A stirred slurry of 2-amino-4-phenylquinoline (22 g.) in concentrated hydrochloric acid (50 ml.) was treated dropwise at 0° C. or below with sodium nitrite (7.0 g.) in cold water (35 ml.). The mixture was stirred for 0.5 hours at about 0° C. Stannous chloride dihydrate (56.7 g.) in cold concentrated hydrochloric acid (70 ml.) was added at 0° C. dropwise. The slurry was refrigerated overnight, filtered, and the precipitate was washed with saturated sodium chloride. The filtered solid was treated with excess concentrated sodium hydroxide solution and the hydrazine was extracted into ethyl acetate. The organic extract was washed, dried, decolorized and saturated with dry hydrogen chloride. On removal of the solvent, 2-hydrazino-4-phenylquinoline dihydrochloride was obtained. This compound was reacted with acrylonitrile using the same procedure described in Example 1.
Workup
- waitThe slurry was refrigerated overnight
- filtrationfiltered
- washthe precipitate was washed with saturated sodium chloride
- additionThe filtered solid was treated with excess concentrated sodium hydroxide solution
- extractionthe hydrazine was extracted into ethyl acetate
- extractionThe organic extract
- washwas washed
- customdried
- customOn removal of the solvent
Sources & evidence
- ORD record
- ord-a8ffbbfc220c46899f323cc13aada42c
- Source dataset
- uspto-grants-1983_10
- Patent number
- US04407803
Reaction notes
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