N-Phenylquinolin-6-amine → HCID 57589733, compound
Reaction equation
[NH:1]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.[Pt](=O)=O>[C:2]1([NH:1][C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[NH:14][CH2:13][CH2:12][CH2:11]3)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 20.4 grams of 6-anilinoquinoline (prepared as described in Buu-Hoi, Royer and Hubert-Habart, J. Chem. Soc., 1956, 2048-2051) in 400 mL of acetic acid containing 1.3 grams of platinum(IV) oxide was hydrogenated at 30 psi for 4.2 hours on a Parr low-pressure hydrogenator. The solution was filtered; and the filtrate was neutralized with 6N aqueous sodium hydroxide. The aqueous phase was extracted three times with dichloromethane. The combined dichloromethane layers were washed with 6N aqueous sodium hydroxide followed by brine. The dichloromethane layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to yield 20.4 grams of a dark residue. The dark residue was recrystallized from 95% ethanol to yield 15.2 grams of the desired product as a grey solid. 1H NMR (CDCl3) δ 7.2 (m, 2H), 6.8 (m, 4H), 6.45 (d, 1H), 5.35 (bs, 1H), 3.4 (bs, 1H), 3.25 (t, 2H), 2.75 (t, 2H), 1.95 (p, 2H).
Workup
- filtrationThe solution was filtered
- extractionThe aqueous phase was extracted three times with dichloromethane
- washThe combined dichloromethane layers were washed with 6N aqueous sodium hydroxide
- dry with materialThe dichloromethane layer was dried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-95048697cb86400084462103892b86f1
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07501386B2
Reaction notes
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