2-Amino-5-chloro-2′-fluorobenzophenone

YELLOW FINE POWDER

General procedure: A mixture of 2-aminoaryl ketones 1 (0.50 mmol), beta-ketoesters/ketones 2 (1.0 mmol), and magnesium chloride (MgCl2 · 6H2O, 20.3 mg, 0.10 mmol) in EtOH (3 mL) was added into a Schlenk flask (25 mL) and the mixture was stirred at 80 C until the reaction was finished. Then the solvent was evaporated under reduced pressure and the residue was purified by column chromatography.General procedure: A mixture of 1 (2 mmol) 2 (2.1 mmol) and L-proline(10mol%) was taken in 50mL Erlenmeyer Flask and subjectedto microwave irradiation at 450W level for a period of 7-8min at 5 sec intervals. The completion of the reaction wasmonitored by TLC. The reaction mixture was cooled to RTand poured into ice cold water (50 mL). The separated solidwas filtered, washed with water and dried to obtain crude 3.It was recrystallized from hexane-ethyl acetate to obtainpure 3.General procedure: HCl (10 N, 3.0 cm3) was added to 10 mmol of aminoarylketone and 15 cm3 of distilled water followed by 22 mmol of diketone; the reaction mixture was allowed tobe placed at room temperature for appropriate time without agitation. The completion of reaction was confirmed by TLC. Reaction mixture was basified with 10 cm3 20% NaHCO3 and the solid was filtered and washed with 20 cm3 water followed by 1.5 cm3 diethyl ether, then dried over air.General procedure: HCl (10 N, 3.0 cm3) was added to 10 mmol of aminoarylketone and 15 cm3 of distilled water followed by 22 mmol of diketone; the reaction mixture was allowed tobe placed at room temperature for appropriate time without agitation. The completion of reaction was confirmed by TLC. Reaction mixture was basified with 10 cm3 20% NaHCO3 and the solid was filtered and washed with 20 cm3 water followed by 1.5 cm3 diethyl ether, then dried over air.General procedure: HCl (10 N, 3.0 cm3) was added to 10 mmol of aminoarylketone and 15 cm3 of distilled water followed by 22 mmol of diketone; the reaction mixture was allowed tobe placed at room temperature for appropriate time without agitation. The completion of reaction was confirmed by TLC. Reaction mixture was basified with 10 cm3 20% NaHCO3 and the solid was filtered and washed with 20 cm3 water followed by 1.5 cm3 diethyl ether, then dried over air.A mixture of To a solution of 2-amino-5-chloro-2?-fluorobenzophenone 1a (0.15 g, 0.6 mmol) in dry CH2Cl2(10 mL) at 0 C was added dropwise bromoacetyl bromide (0.12 mL, 2.3 mmol). After stirring the mixture at 0 C for 4 h, the reaction solution was quenched with ammonia solution 5% (30 mL) and extracted with CH2Cl2(2 × 25 mL). The combined organic layers were dried over MgSO4, concentrated in vacuum, and the white product was washed with diethyl ether and cold methanol for further purification. Yield: 0.2 g (0.54 mmol, 90%); pale white solid. Mp 131-133 C. IR (numax, KBr): 1648, 1690 cm- 1 2(C=O), 3014 cm- 1 (-CH2), 3387 cm- 1 (N-H). 1HNMR (250 MHz, CDCl3, deltappm): 4.24 (s, 2H), 7.17-7.35 (m, 2H), 7.49-7.64 (m, 4H), 8.72 (d, 1H, J = 7.5), 11.96 (s, 1H). 13CNMR (62.5 MHz, CDCl3, deltappm): 43.2, 116.5, 116.8, 122.5, 124.6, 124.7, 124.9, 126.5, 126.7, 128.6, 130.5, 130.6, 133.1, 133.1, 133.9, 134.1, 135.0, 138.2, 157.6, 161.6, 165.7, 195.5.

A starting material for the synthesis of diazepam and other benzodiazepines

Molecular Weight:249.67
XLogP3:3.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:249.0356698
Monoisotopic Mass:249.0356698
Topological Polar Surface Area:43.1
Heavy Atom Count:17
Complexity:287
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes