Water → [4-(2-furyl)phenyl]amine hydrochloride
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][CH:12]=[CH:13][CH:14]=2)=[CH:6][CH:5]=1)([O-])=O.O>C(O)C>[O:11]1[CH:12]=[CH:13][CH:14]=[C:10]1[C:7]1[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a suspension of 2-(4-nitrophenyl)furan (0.378 g, 2 mmol, prepared according to the method of Heterocycles, 1990, 31, 1951) in ethanol (20 mL) was heated to 70° C. and added stannous chloride dihydrate (2.26 g, 10 mmol) and the mixture was stirred for 2 hours. The reaction mixture was cooled to room temperature and poured into water (50 mL), the whole was extracted with ethyl acetate (30 mL×2). The organic layer was dried over Na2SO4, filtered through celite and concentrated to give the crude subtitle compound (0.35 g).
Workup
- customprepared
- temperatureThe reaction mixture was cooled to room temperature
- extractionthe whole was extracted with ethyl acetate (30 mL×2)
- dry with materialThe organic layer was dried over Na2SO4
- filtrationfiltered through celite and
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-6b3e14b48a444c749b294474fc543b2a
- Source dataset
- uspto-grants-2001_09
- Patent number
- US06294558B1
Reaction notes
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