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

HRID 1939139
Notes
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Reaction equation

HRID 1939139 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 3338121H-Isoindole-1,3(2H)-dione, 2-(3-amino-4-chlorophenyl)-HCID 516892Sodium BicarbonateHCID 522863Isopentyl 2-bromopropanoate

Product 1

HCID 21467014Isopentyl 2-[(2-Chloro-5-phthalimidophenyl)amino]propionateYield 65.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

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

  1. washthe reaction mixture was washed successively with water
  2. dry with materiala saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes