N,N-dimethyl-3-(4-nitrophenoxy)propan-1-amine → 4-(3-(Dimethylamino)propoxy)aniline
Reaction equation
[CH3:1][N:2]([CH3:16])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=1>C(O)C.[Pd]>[CH3:16][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([NH2:13])=[CH:11][CH:12]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
4-(3-(dimethylamino)propoxy)nitrobenzene (4.4 g, 19.6 mmol) was hydrogenated over Pd (10% on C, 0.4 g) in ethanol (50 ml) for 16 h. The catalyst was filtered off and the solvent removed under reduced pressure to afford the title compound as a brown oil. MS (m/z)=195.3 (M+H+); Calc'd for C11H18N2O=194.28.
Workup
- filtrationThe catalyst was filtered off
- customthe solvent removed under reduced pressure
Sources & evidence
- ORD record
- ord-18b5d0b13591476ebaa13d08e611dded
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07776869B2
Reaction notes
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