4-Bromoisatoic anhydride

White solid

2-Amino-1-ethyl-4-oxo-7-[4-(3-pyridin-3-ylmethylureido)phenyl]-1, 4-dihydroquinoline-3-carboxylic Acid Amide (No. 57)7.1: 7-Bromo-1H-benzo[d][1, 3]oxazine-2, 4-dione In a 250 ml round-bottomed flask, under a nitrogen atmosphere, 5.0 g (23.1 mmol) of 2-amino-4-bromobenzoic acid are dissolved in 50 ml of anhydrous dioxane. The temperature of the mixture is reduced to 0° C. by means of an ice bath. 2.3 g (7.6 mmol) of triphosgene are added dropwise. The ice bath is replaced with an oil bath and the mixture is refluxed for 16 h. After a return to ambient temperature, water (100 ml) is added and the precipitate formed is filtered off, washed with EtStep 1 : To a solution of 2-amino-4-bromobenzoic acid (4 g, 18.51 mmol) in 1, 4-dioxane (40 mL) was added bis(trichloromethyl)carbonate in 1, 4-dioxane (1.81 g, 6.11 mmol) drop wise at 0 °C. The reaction mixture was stirred at 110 °C for 16 h. The solvent was evaporated under reduced pressure and washed with n-hexane to afford 7-bromo-lH- benzo[d][l, 3]oxazine-2, 4-dione (4.3 g, 95.8percent LC-MS 97percent).To a solution of 2-amino-4-bromobenzoic acid (4 g, 18.51 mmol) in 1, 4-dioxane (40 mL) was added bis(trichloromethyl)carbonate in 1, 4-dioxane (1.81 g, 6.11 mmol) drop wise at 0° C. General procedure: A 500 mL single neck round-bottomed flask equipped with a football-shaped PTFE stirring bar (16 mm × 37 mm) was chargedwith 2-amino-5-bromobenzoic acid (10.0 g, 46.3 mmol, 1.0 equiv) followed by the addition of tetrahydrofuran (230 mL, 0.2 molar) and solid triphosgene (13.7 g, 46.3 mmol, 1.0 equiv)resulting in a suspension. The reaction vessel was placed into afitted metal heating mantle and the neck was equipped with a24/40 Liebig condenser. The suspension was stirred (500 rpm)and the heating mantle set to 70 °C. The suspension becamehomogenous before a white solid precipitated out after about30 minutes at 70 °C. The heterogeneous reaction mixture wasaged for 12 hours then cooled to room temperature (25 °C). Theslurry was poured into a 600 mL beaker equipped with overheadmechanical stirrer (PTFE 75 mm paddle) containing250 mL of deionized water. With vigorous stirring, the mixturebecame homogenous followed by precipitation of a pale whitesolid. The solid was collected by vacuum filtration on aBüchner funnel (7.6 cm diameter) with Whatman 1 filter paper(70 mm) and air pulled through for 5 minutes. The material was transferred to a 250 mL Erlenmeyer flask equipped with cylindricalstir bar and 50 mL of methanol was added. The slurrywas stirred for 10 minutes and then collected by vacuum filtration.The filter cake was dried under vacuum (0.1 mmHg at 25 °C) for 12 hours to afford 9b as a white powder (90percent yield).The 2-amino-4-bromobenzoic acid (10.0g, 46 . 3mmol) dissolved in tetrahydrofuran (100 ml) in, adding triphosgene (4.54g, 15 . 3mmol), under the protection of nitrogen is heated to 80 °C stirring overnight. Cooling to room temperature, the reaction solution the ice water (120 ml) in, filtering, the filter cake are sequentially water, ether washing, drying, to obtain brown solid (7.60g, 68.0percent).

Molecular Weight:242.03
XLogP3:1.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:240.93746
Monoisotopic Mass:240.93746
Topological Polar Surface Area:55.4
Heavy Atom Count:13
Complexity:256
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes