7-CHLOROISATIN

Orange powder

In a 250 mL four-necked flask, (0.025 mol) of N- (2-chlorophenyl) -2-isonitrosonoacetanilide was added portionwise to 15 mL of concentrated sulfuric acid, Feeding process temperature does not exceed 50 , Feeding complete, Was slowly stirred reaction warmed to 85 , Reaction completed, The reaction solution was quenched with vigorous stirring into 100 mL of crushed ice, After stirring for 1 hour, filter, dry, Methanol to obtain 2.97 g of 7-chloroisatin as a pale yellow solid (yield 65percent).General procedure: 4.2 General procedure for the synthesis of 5 and 10a–g: (a) A 500 ml, three-necked, round-bottomed flask fitted with a condenser and a thermometer was charged with chloral hydrate (16.50 g, 0.1 mol) and 220 ml of water. Then anhydrous sodium sulfate (15.00 g), aniline derivative (0.1 mol), HCl solution (5.2 percent, 70 ml), and hydroxylamine hydrochloride (20.81 g, 0.3 mol, in 95 ml of water) were added in successively. After being heated to reflux for 1 h, the reaction mixture was cooled to room temperature. The intermediate compound (anilide derivative) was collected by filtration and dried, which was used for next step without further purification. (b) A 100 ml, three-necked, round-bottomed flask fitted with a thermometer was charged with concentrated sulfuric acid (10 equiv). After heating to 50 °C with stirring, the dried product (1 equiv) from the above step was added in over a period of 20 min. The resulting solution was heated to 65 °C and kept for 1 h and then cooled down to room temperature with an ice bath. The precipitate was filtered out and dried to get the target compounds. The dried product from the above step (15.4 g, 0.095 mol) was added into concentrated sulfuric acid (50 ml) in a period of 20 min at 50 °C. Then the resulted mixture was heated to 65 °C and kept for 1 h. The mixture was poured into ice water. The precipitate in the mixture was filtered out and dried.General procedure: To a solution of 120mL water, chloral hydrate (8.93g, 0.054mol), anhydrous sodium sulfate (130g, 0.40mol), aniline or substituted aniline 5 (0.05mol), hydroxylammonium chloride (10.98g, 0.158mol) and concentrated hydrochloric acid (43mL) were added respectively. Subsequently, the resulting suspension was heated to 90°C for 5min and cooled to room temperature. After filtration and washing with water (2×20mL), the crude material was obtained. The crude was added in batches to a 250mL, three mouth flask filled with concentrated sulfuric acid (32.6mL) at the temperature of 65°C and then heated up to 80°C for 20min. The reaction solution was cooled to room temperature and poured onto 500g of ice water and stirred vigorously for 4h. Intermediates 6a–i were isolated by filtration, washing with water, and recrystallization from ethanol with yields from 25.7percent to 73.2percent.

Molecular Weight:181.57
XLogP3:1.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:180.9930561
Monoisotopic Mass:180.9930561
Topological Polar Surface Area:46.2
Heavy Atom Count:12
Complexity:241
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes