1-{2-Hydroxy-3-propyl-4-[3-(4-nitrophenoxy)propoxy]phenyl}ethanone → 1-{2-Hydroxy-3-propyl-4-[3-(4-aminophenoxy)propoxy]phenyl}ethanone
Reaction equation
[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([O:11][CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=2)[CH:5]=[CH:4][C:3]=1[C:25](=[O:27])[CH3:26]>C(O)C.CN(C)C=O.[Pd]>[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([O:11][CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:17]=[CH:18][C:19]([NH2:22])=[CH:20][CH:21]=2)[CH:5]=[CH:4][C:3]=1[C:25](=[O:27])[CH3:26]Participants
5
Procedure
1-{2-Hydroxy-3-propyl-4-[3-(4-nitrophenoxy)propoxy]phenyl}ethanone (19.6 g) was dissolved in a mixture of ethanol (300 ml) and dimethylformamide (100 ml), to which was added under nitrogen, a slurry of palladium on charcoal catalyst (1.0 g, 5%) in ethanol (50 ml). The suspension was then hydrogenated on a Parr at 60 psi and room temperature for 90 minutes. The suspension was filtered over Celite (registered Trade Mark), washed with ethanol and the filtrate evaporated under reduced pressure to a brown oil, which was triturated with water and filtered to give a brown solid. The solid was recrystallised from ethanol with charcoal to give a white solid, m.p. 75°-77° C.
Workup
- additionwas added under nitrogen
- filtrationThe suspension was filtered over Celite (registered Trade Mark)
- washwashed with ethanol
- customthe filtrate evaporated under reduced pressure to a brown oil, which
- customwas triturated with water
- filtrationfiltered
- customto give a brown solid
- customThe solid was recrystallised from ethanol with charcoal
- customto give a white solid, m.p. 75°-77° C.
Sources & evidence
- ORD record
- ord-0e2bc2c7b9d94cd786990898bba825f5
- Source dataset
- uspto-grants-1987_06
- Patent number
- US04675333
Reaction notes
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