Sodium Hydroxide → 4-methylquinolin-3-amine
Reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-])=O.O.O.[Sn](Cl)Cl.[OH-].[Na+]>Cl.O>[NH2:12][C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[CH3:1])=[CH:10][CH:9]=[CH:8][CH:7]=2Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
A solution of 4-methyl-3-nitroquinoline (500 mg, 2.66 mmol) in conc. HCl (10 mL) was heated to 50° C. Tin (II) chloride dihydrate (1.5 g, 6.6 mmol) was added. The mixture was stirred at 50° C. overnight. The mixture was diluted with water (20 mL). The mixture was adjusted to pH 9 by addition of 5N aqueous sodium hydroxide. The mixture was cooled to 4° C. and extracted twice with ethyl acetate (30 mL). The combined extracts were washed with ice-cold water (40 mL) and dried over anhydrous Na2SO4, filtered, and concentrated to give 3-amino-4-methylquinoline (340 mg, 80%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 8.42 (s, 1H), 7.89-7.91 (m, 1H), 7.79-7.82 (m, 1H), 7.44-7.38 (m, 2H), 3.77 (br s, 2H), 2.37 (s, 3H).
Workup
- temperatureThe mixture was cooled to 4° C.
- extractionextracted twice with ethyl acetate (30 mL)
- washThe combined extracts were washed with ice-cold water (40 mL)
- dry with materialdried over anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-2fd6b590492a4d548416f424a8b160c4
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08927577B2
Reaction notes
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