6-Bromoisatin

Orange Powder

Step 2: 6-Bromo-lH-indole-2, 3-dioneTo the concentrated sulfuric acid (275 mL) at 50 °C was added N-(3-Bromo- phenyl)-2-hydroxyimino-acetamide (55 g, 0.2272 mol). The temperature was raised to 90 °C and maintained for 3 h. The reaction mixture was added to ice cold water to get yellow precipitate. The precipitate was filtered and dried to get the title compound as a yellow solid [50 g, 98percent]. This material was taken to the next step without any further purification6-bromo-1 /-/-indole-2, 3-dioneTo sulfuric acid (2.3 L) at 60°C was added A/-(3-bromophenyl)-2- (hydroxyimino)ethanamide (1 10 g, 456.43 mmol) portionwise over 30 minutes such that the temperature of the reaction mixture did not exceed 65°C. The mixture was heated to 80°C for 15 minutes, cooled to 70°C, and poured onto crushed ice. The ice mixture was allowed to stand for 1 h. Solids were collected by filtration, washed with water, and dried. The crude material was dissolved in a solution of NaOH (58 g) in water at 60°C and acidified with acetic acid. After standing for 0.5 h, the mixture was cooled to 35°C. Solids were collected by filtration and washed with a minimal amount of water. The filter cake was set aside. The filtrate was acidified with concentrated HCI and allowed to stand for 2 h at 5°C. Solids were collected by filtration and washed with water. The combined filter cakes were dried in vacuo to afford 6-bromo-1 H-indole-2, 3-dione (33 g, 32percent yield). To concentrated sulfuric acid (275 mL) at 50° C. was added N-(3-bromo-phenyl)-2-hydroxyimino-acetamide (55 g, 0.2272 mol). The temperature was raised to 90° C. and maintained for 3 hours. The reaction mixture was added to ice cold water to provide a yellow precipitate. The precipitate was filtered and dried to provide the title compound as a yellow solid (50 g, 98percent). This material was taken for next step without any further purification.Example 59; Preparation of A33; Synthesis of 4-Bromoisatin (K-98) and 6-Bromoisatin (K-99); To a solution chloral hydride (50.0 g, 0.247 mol) in water (237mL) were successively added NaSulfuric acid (1 L) was heated in a 3 L beaker on a hot plate to 60 °C and then removed. The dry isonitrosoacetanilide 2a-f was added in portion with stirring over 30 min so that the temperature did not exceed 65 °C. The mixture was then heated to 80 °C for 15 min, allowed to cool to 70 °C and cooled on ice. The solution was poured onto crushed ice (5 L) and left to stand for 1 h before filtering the orange-red precipitate. The product was washed by stirring with water (400 mL) and filtered to give a mixture of 3a-f and 4a-f. The crude product was dissolved in a solution of NaOH (20 g) in water (200 mL) at 60 °C, and then acidified with acetic acid (60 mL). After standing 0.5 h and cooling to 35 °C, the 4a-4f precipitate was filtered and washed with water (50 mL). The combined filtrate and washings were acidified with conc. HCL (60mL) and, after standing for 2 h at 5 °C, the 3a-f precipitate was filtered off and washed with water (50 mL). Yields: 3a: 27percent, 3b: 14percent, 3c : 29percent, 3d: 22percent, 3e: 33percent, 3f : 31percent, 4a: 56percent, 4b: 64percent, 4c: 53percent, 4d: 59percent, 4e: 49percent, 4f : 51percent.10.00 g (58.13 mmol) of 3-bromoaniline was placed in a 1000 mL round bottom flask, 500 mL of water was added, (45.343 mmol) of anhydrous sodium sulfate and 13.33 g (191.84 mmol) of hydrochloric acid light were added under stirring. Then, 10 mL of a 2 mol / L hydrochloric acid solution was added and stirred at room temperature for 5 min.Finally, 10.58 g (63.95 mmol) of chloral hydrate was added. The reaction mixture was stirred at room temperature for 15 min, then heated at 90 ° C under reflux reaction 2KTLC detection of raw materials disappeared, Then cooled to room temperature, filtered and vacuum dried to give 12.90 g of a pale yellow solid. 0 mL of concentrated sulfuric acid was added to a 100 mL round bottom flask and 12.90 g of a yellow solid was slowly added to concentrated sulfuric acid at 50 ° C and reacted at 65 ° C for 30 min after complete addition.After the reaction, the reaction mixture was cooled to room temperature. The reaction mixture was poured into an ice-water mixture and stirred for 30 minutes. The solid was filtered by suction filtration and dried in a vacuum oven. Petroleum ether: ethyl acetate = To give 4.12 g of 6-bromoindolinedione in a yield of 31.4percent.

Antimicrobial

Molecular Weight:226.03
XLogP3:1.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:224.94254
Monoisotopic Mass:224.94254
Topological Polar Surface Area:46.2
Heavy Atom Count:12
Complexity:241
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes