1H-Isoindole-1,3(2H)-dione, 2-(3-amino-4-chlorophenyl)- → Isopentyl 2-[(2-Chloro-5-phthalimidophenyl)amino]propionate

HRID 1939139Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C:12]3=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]3[C:10]2=[O:19])[CH:5]=[CH:6][C:7]=1[Cl:8].Br[CH:21]([CH3:30])[C:22]([O:24][CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28])=[O:23].C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[Cl:8][C:7]1[CH:6]=[CH:5][C:4]([N:9]2[C:13](=[O:14])[C:12]3=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]3[C:10]2=[O:19])=[CH:3][C:2]=1[NH:1][CH:21]([CH3:30])[C:22]([O:24][CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28])=[O:23]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 1.64 g of N-(3-amino-4-chlorophenyl)phthalimide, 2.68 g of isopentyl 2-bromopropionate, and 0.60 g of sodium hydrogencarbonate was heated at 150° C. for 5 hours while stirring. While the reaction mixture was hot, ethyl acetate was added thereto, and the reaction mixture was washed successively with water and a saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate-hexane=1:8) to give 1.63 g of the title compound (Table 1, Compound No. 5).

Workup

washthe reaction mixture was washed successively with water
dry with materiala saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (ethyl acetate-hexane=1:8)

Sources & evidence

ORD record: ord-4525023e361d4c5783a70d8ef30c3b67
Source dataset: uspto-grants-1997_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05696056

Reaction notes

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