Methyl 2-amino-4-(trifluoromethyl)benzoate

Methyl 2-amino-4-(trifluoromethyl)benzoate

61500-87-6 CAS
Synonyms:	4-trifluoromethyl-2-aminobenzoic acid methyl ester; 2-AMINO-4-TRIFLUOROMETHYL-BENZOIC ACID METHYL ESTER;

1H NMR (DMSO-d6) δ 3.79 (s, 3h), 6.75 (dd, j=1.84, 8.46 hz, 1H), 6.96 (br s, 2h), 7.11 (d, j=0.73 hz, 1H), 7.83 (d, j=8.09 hz, 1H)








13 C NMR PREDICT




COSY PREDICT

SYNTHESIS

Hill; Stanley; Karoglan Williams; Loev; Fowler; McCafferty; Macko; Berkoff; Ladd Journal of Medicinal Chemistry, 1983 , vol. 26, # 6 p. 865 - 869

ELI LILLY AND COMPANY Patent: WO2006/2342 A1, 2006 ; Location in patent: Page/Page column 55-56 ;

European Journal of Medicinal Chemistry, , vol. 40, # 9 p. 897 - 907



https://www.google.com/patents/WO2006002342A1?cl=en

Preparation of Methyl 2-amino-4-trifluoromethylbenzoate.

Add a solution of methyl 2-nitro-4-trifluoromethylbenzoate (106 g, 425 mmol) in ethyl acetate (2.2 L) to a slurry of 10% palladium on carbon (11.0 g) in ethyl acetate (200 mL) and stir the suspension at room temperature under an atmosphere of hydrogen at 60 psi for 3 h. Filter the suspension through a pad of Celite® and wash the pad with additional ethyl acetate. Remove the solvents under reduced pressure and purify the residue by column chromatography on silica gel, eluting with isohexane/ethyl acetate (9:1), to provide the title compound as a white crystalline solid (84 g, 95%). 
¹H NMR (300 MHz, CD₃OD)
 δ 7.93 (d, / = 8.48 Hz, IH), 
7.06 (s, IH), 
6.78 (s, IH), 
4.86 (s, 3H), NH2  MAYBE
3.89 (s, 3H).