2-amino-alpha,alpha,alpha-trifluoro-p-creso synthesis
- Product Name:2-amino-alpha,alpha,alpha-trifluoro-p-creso
- CAS Number:454-81-9
- Molecular formula:C7H6F3NO
- Molecular Weight:177.12
400-99-7
454-81-9
The general procedure for the synthesis of 2-amino-4-trifluoromethylphenol from 2-nitro-4-trifluoromethylphenol was as follows: 2-nitro-4-trifluoromethylphenol (340 μL, 2.41 mmol) was dissolved in methanol (50 mL), and catalytically hydrogenated at room temperature and atmospheric pressure using a 10% Pd/C catalyst cartridge through an H-Cube hydrogenation reactor. Upon completion of the reaction, the reaction solution was concentrated under reduced pressure to give 2-amino-4-trifluoromethylphenol (438 mg, 100% yield) as a light brown solid. Mass spectrum (chemical ionization, m/z): [M+H]+ 178, [M-H]- 176; 1H NMR (CDCl3): δ 6.96 (d, J=2.0 Hz, 1H), 6.89-6.94 (m, 1H), 6.74 (d, J=8.2 Hz, 1H), 4.10 (br s, 2H).
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454-81-9
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Yield: 83%
Reaction Conditions:
in ethanol
Steps:
117.a a)
a) Preparation of 2-amino-4-trifluoromethylphenol A mixture of 4-trifluoromethyl-2-nitrophenol(1.0 g, 4.8 mmol) and tin (II) chloride (5.4 g, 24.2 mmol) in ethanol(150 mL) was heated at 80° C. under argon. After 2 hours, the starting material had disappeared and the solution was allowed to cool down and then poured into ice. The pH was made slightly basic (pH7-8), by addition of solid NaOH, before being extracted with ethyl acetate. The organic phase was washed with brine, dried over MgSO4 and filtered. The solvent was evaporated and chromatography of the resulting solid on silica gel (4% MeOH/CH2 Cl2) gave the desired product(708 mg, 83%). 1 H NMR (CD3 OD): δ 6.87 (s, 1H), 6.80 (d, 1H), 6.69 (d, 1H).
References:
SmithKline Beecham Corporation US5886044, 1999, A
400-99-7
184 suppliers
$19.00/5g
454-81-9
128 suppliers
$22.00/250mg
121-17-5
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454-81-9
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402-45-9
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454-81-9
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$22.00/250mg
400-98-6
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$10.00/5g
454-81-9
128 suppliers
$22.00/250mg