4-Chlorophthalimide

slight yellow crystalline powder

General procedure: 0.01g of MnO2 catalyst, 0.5mmol of 1-indanone, 0.2g of ammonia water (25wtpercent) and 2g of chlorobenzene were added to a stainless steel autoclave with a polytetrafluoroethylene inner liner.The temperature was raised to 110 by automatic temperature controller, 0.6MPa oxygen was added and the reaction was continued for 4h. The pressure was kept constant during the reaction.The reaction product was analyzed using GC-MS with a phthalamide yield of 85percent.6: A suspension of 4-amino-phthalimide 5 (6.48 g, 39.9 mmol) in hydrochloric acid (18percent, 120 mL) was cooled to 0 °C. A solution of sodium nitrite (3.25 g, 47.2 mmol) in HTo a solution of intermediate compound 3 (0.037 mol) in 20 ml of concentrated hydrochloric acid was added slowly to a solution of sodium nitrite (0.039 mol) in 15 ml of water under ice-cooling. The temperature of the control solution was not more than 5 ° C. After adding, the mixture was stirred for 30 minutes under ice bath, and the insoluble matter was filtered off. The filtrate was slowly added to a mixture of cuprous chloride (0.3737 mol) in 10 ml of concentrated hydrochloric acid, stirred and added at 70 ° C until no more bubbles were allowed to stand for 12 hours, filtered to give a yellow solid, The filter cake was washed with water and recrystallized from ethanol to give intermediate 4 as a yellow solid in 58.6percent yieldNitrogen protected, cooled to -15 C, 0.60 g (2.5 mmol) of 3-n-butyl-5-chloro-3-hydroxyisoindolin-1-one and 3-n-butyl-6-chloro-3 -A mixture of hydroxyisoindolin-1-one was dissolved in 30 ml of DCM, and then 2.9 g (25.0 mmol) of triethylsilane and 1.1 g (7.5 mmol) of boron trifluoride ether solution were added, and the temperature was returned to room temperature, and the reaction was performed. Overnight, TLC showed the reaction was complete.The reaction solution was poured into a 5% sodium solution, extracted with DCM, dried, concentrated, and subjected to silica gel column chromatography. A mixed eluent of ethyl acetate and petroleum ether was used as the eluent (the volume ratio of ethyl acetate and petroleum ether was 1: 1), get:3-n-butyl-5-chloroisoindolin-1-one (A) (small polar point, first eluted component), yield 35.7%.3-n-butyl-6-chloroisoindolin-1-one (B) (a point of great polarity, the second elution component), with a yield of 37.5%.Protected with nitrogen, cooled to 0 C in an ice bath, added 1.0 g (5.5 mmol) of 5-chloroimphthalate to the reaction flask, added 30 ml of DCM, and contained 1.3 g (8.62 mmol) of n-butylmagnesium bromide. THF solution (8ml) was added dropwise to the reaction flask, and the reaction was performed in an ice bath for 1.5 hours. TLC showed no reaction. The temperature was raised to room temperature, and 1.5 equivalents of n-butyl magnesium bromide Grignard reagent were added. The reaction was performed for 2.5 hours. The reaction was shown to be complete. The reaction wasquenchedwith saturated NH4Cl, extracted with DCM, dried, concentrated, and subjected to silica gel column chromatography. A mixture of ethyl acetate and petroleum ether was used as the eluent (the volume ratio of ethyl acetate and petroleum ether was 1: 1), to obtain a mixture of 3-n-butyl-5-chloro-3-hydroxyisoindolin-1-one and 3-n-butyl-6-chloro-3-hydroxyisoindolin-1-one, Yield 45.5%,

Molecular Weight:181.57
XLogP3:1.8
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