2-Amino-5-chlorobenzophenone

Chemical compound, benzodiazepine precursor 2-Amino-5-chlorobenzophenone 12870 2-Amino-5-chlorobenzophenone 2-Amino-5-chlorobenzophenone.svg (2-Amino-5-chlorophenyl)(phenyl)methanone 2-amino-5-chlorobenzophenone 2-Benzoyl-4-chloroaniline 719-59-5 correct CAS 12339 211-949-7 FR80014ZBT 1417425 12870 C1=CC=C(C=C1)C(=O)C2=C(C=CC(=C2)Cl)N 1S/C13H10ClNO/c14-10-6-7-12(15)11(8-10)13(16)9-4-2-1-3-5-9/h1-8H,15H2 ZUWXHHBROGLWNH-UHFFFAOYSA-N 13 10 1 1 1 07 Warning 315 319 335 261 264 264+265 271 280 302+352 304+340 305+351+338 319 321 332+317 337+317 362+364 403+233 405 501 2-Amino-5-chlorobenzophenone is a substituted benzophenone that can be used in the synthesis of benzodiazepines. Chemistry 2-Amino-5-chlorobenzophenone is a substituted derivative of benzophenone, where the hydrogen atom at the 2 position has been replaced by an amino group (–NH2) and the one at the 5 position replaced with a chlorine atom. Synthesis center|thumb|619x619px|Synthesis of 2-Amino-5-chlorobenzophenone in two steps from 4-nitrochlorobenzene. 2-amino-5-chlorobenzophenone can be synthesized in two steps from 4-nitrochlorobenzene.Granik V. G. Pechenina V. M. Mukhina N. A. January 1991 2,1-Bensoidoxazoles [anthranils]. Synthesis and opening of the isoxazole ring (review) https://link.springer.com/10.1007/BF00766367 Pharmaceutical Chemistry Journal en 25 1 48–59 10.1007/BF00766367 0091-150X In the first step 4-nitrochlorobenzene is condensed with phenylacetonitrile in alkaline methanol.Davis R. B. Pizzini L. C. November 1960 Condensation of Aromatic Nitro Compounds with Acrylacetonitriles. 1,2 II. Some p-Substituted Nitrobenzenes https://pubs.acs.org/doi/abs/10.1021/jo01081a015 The Journal of Organic Chemistry en 25 11 1884–1888 10.1021/jo01081a015 0022-3263 This proceeds with the loss of cyanide and water to produce 5-chloro-3-phenylanthranil. In a subsequent step the isoxazole ring undergoes reductive cleavage to furnish the benzophenone. This reduction can be conducted with iron in hydrochloric acidDD 278473A3 Process for the preparation of 2-aminobenzophenones 1990-05-09 Niegel Nauwald https://patents.google.com/patent/DD278473A3 or by catalytic hydrogenation in the presence of palladiumWalker Gordon May 1962 Hydrogenation of Anthranils https://pubs.acs.org/doi/abs/10.1021/jo01052a098 The Journal of Organic Chemistry en 27 5 1929–1930 10.1021/jo01052a098 0022-3263. Synthesis of benzodiazepines 2-Amino-5-chlorobenzophenone and its derivatives can be used to produce benzodiazepines, a few examples are listed below; Prazepam Prazepam can be produced by the acylation of 2-amino-5-chlorobenzophenone with cyclo-propanecarbonyl chloride and triethylamine, 2-cyclopropylmethylamino-5-chlorobenzhydrol is then obtained by using lithium aluminium hydride as a reducing agent, this product is then oxidized by using manganese dioxide. The resulting compound goes another acylation reaction using phthalimidoacetyl chloride and finally treated with hydrazine hydrate to produce prazepam.Prazepam 143–155 https://www.ncbi.nlm.nih.gov/books/NBK423852/ Some Pharmaceutical Drugs https://publications.iarc.who.int/Book-And-Report-Series/Iarc-Monographs-On-The-Identification-Of-Carcinogenic-Hazards-To-Humans/Some-Pharmaceutical-Drugs-1996 IARC Monographs on the Evaluation of Carcinogenic Risks to Humans 1996 66 978-92-832-1266-9 9097122 7681523 Lorazepam Lorazepam can be made using 2-amino-2′,5-dichlorobenzophenone (a derivative of 2-amino-5-chlorobenzophenone), which is first reacted with hydroxylamine, the obtained product is then reacted with chloroacetyl chloride to give 6-chloro-2-chlormethyl-4-(2′-chlorophenyl)quinazolin-3-oxide, a reaction with methylamine produces ring expansion and rearrangement, which forms 7-chloro-2-methylamino-5-(2′-chlorphenyl)-3H-1,4-benzodiazepin-4-oxide, acetylation with acetic anhydride gives a product which goes under hydrolysis by reacting it with hydrochloric acid, this gives 7-chloro-5-(2′-chlorophenyl)-1,2-dihydro-3H-1,4-benzodiazepin-2-on-4-oxide, a second reaction with acetic anhydride gives 7-chloro-1,3-dihydro-3-acetoxy-5-(2′-chlorphenyl)-2H-benzodiazepin-2-one, the last step involves hydrolysis of this product under sodium hydroxide to give lorazepam.Vardanyan R.S. Hruby V.J. Synthesis of Essential Drugs Anxiolytics (Tranquilizers) 2006 69–82 10.1016/B978-044452166-8/50005-4 978-0-444-52166-8 Chlordiazepoxide To make chlordiazepoxide, 2-amino-5-chlorobenzophenone is first reacted with hydroxylamine, the resulting product is then reacted with chloracetyl chloride in acetic acid, resulting in 6-chloro-2-chloromethyl-4-phenylquinazolin-3-oxide, reaction with methylamine gives chlordiazepoxide. References Category:2-Aminobenzophenones Category:Chlorobenzene derivatives Category:Anilines