Acetic Acid → 2,5-Dimethyl-4-[(2-propylcyclopropyl)methoxy]phenylamine
Reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([CH3:11])=[CH:4][C:3]=1[O:12][CH2:13][CH:14]1[CH2:16][CH:15]1[CH2:17][CH2:18][CH3:19].C(O)(=O)C>[Fe].O>[CH3:11][C:5]1[CH:4]=[C:3]([O:12][CH2:13][CH:14]2[CH2:16][CH:15]2[CH2:17][CH2:18][CH3:19])[C:2]([CH3:1])=[CH:7][C:6]=1[NH2:8]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 1.58 g of 2,5-dimethyl-4-nitro-1-[(2-propylcyclopropyl)methoxy]benzene, 1.68 g of iron powder, 20 mL of acetic acid and 20 mL of water was stirred at 80° C. for 1 hour. The reaction mixture was cooled to around room temperature, and then concentrated under reduced pressure. The resulting residue was converted into basic with an aqueous 1 N sodium hydroxide solution, then ethyl acetate was added, and the mixture was filtered. The filtrate was extracted with ethyl acetate, and then the organic layer was washed with water and saturated salt water, and dried over anhydrous magnesium sulfate. The resulting residue was subjected to silica gel column chromatography to obtain 0.90 g of 2,5-dimethyl-4-[(2-propylcyclopropyl)methoxy]phenylamine.
Workup
- temperatureThe reaction mixture was cooled to around room temperature
- concentrationconcentrated under reduced pressure
- additionethyl acetate was added
- filtrationthe mixture was filtered
- extractionThe filtrate was extracted with ethyl acetate
- washthe organic layer was washed with water and saturated salt water
- dry with materialdried over anhydrous magnesium sulfate
Sources & evidence
- ORD record
- ord-ff119da096dc42fa812ec7490339f4c1
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09309191B2
Reaction notes
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