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CAS No. : | 69411-05-8 | MDL No. : | MFCD02684210 |
Formula : | C7H5ClF3N | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OVENUGPMQDFGLE-UHFFFAOYSA-N |
M.W : | 195.57 | Pubchem ID : | 3017933 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H319 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With tin(ll) chloride; In ethyl acetate; for 3.0h;Heating / reflux; | To a stirred mixture of l-chloro-3-nitro-5-(trifluoromethyl)benzene (2.90 g, 12.9 mmoL) in 120 mL of EtOAc, was added SnCl2 dihydrate (12.0 g, 51.6 mmoL). This mixture was heated to reflux for 3 h and cooled to room temperature. Next, the mixture was diluted with 100 mL of EtOAc and washed with 2.5N NaOH solution (Ix 150 mL). The aqueous layer was separated and extracted with EtOAc (Ix 200 mL). Combined EtOAc layers were washed with brine (Ix 40 mL), dried (MgSO4), filtered and concentrated in vacuo to give 2.51 g of Preparation 65A (3- chloro-5-(trifluoromethyl)aniline) as a yellow solid in quantitative yield.[00495] HPLC: 2.57 min (RT) (Chromolith SpeedROD column 4.6 x 50 mm, 10- 90% aqueous MeOH over 4 minutes containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm). MS (ES): m/z=196 [M+H]+. |
In methanol; aluminum nickel; | Step 2 92 g (0.408 mol) of <strong>[401-93-4]5-chloro-3-trifluoromethyl-nitrobenzene</strong> in 1 l of methanol are hydrogenated in the presence of 10.17 g of Raney nickel. The reaction mixture is filtered through Celite/activated carbon and the residue washed with methanol. Concentration of the filtrate by evaporation yields the oily 5-amino-3-chloro-benzotrifluoride; 1H-NMR (DMSO-d6) delta6.80 (m, 3H), 5.92 (s, H2N). | |
In methanol; aluminum nickel; | 111b 5-Amino-3-chloro-benzotrifluoride In the presence of 10.17 g of Raney nickel, 92 g (0.408 mol) of <strong>[401-93-4]5-chloro-3-trifluoromethyl-nitrobenzene</strong> are hydrogenated in 1 liter of methanol. The reaction mixture is filtered over Celite/activated carbon and the residue is washed with methanol. Concentration of the filtrate by evaporation yields the oily title compound: 1H-NMR (DMSO-d6) 6.80 (m, 3H), 5.92 (s, H2N); FAB-MS (M+H)+=196. |
b. 3-Chloro-5-trifluoromethylaniline Using a procedure similar to that described in Example 20a except starting with <strong>[401-93-4]3-chloro-5-trifluoromethylnitrobenzene</strong>, the title compound was obtained (77%) as an amber oil; MS(CI): 196 (M+H). 250-MHz 1 H NMR (DMSO-d6): 6.82 (s, 1H), 6.79 (s, 1H), 6.77 (s, 1H), 5.94 (s, 2H). |
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