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6-Chloro-2,3-dihydro-1H-isoindol-1-one → HCID 57753529, compound

HRID 1931026
Notes
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Reaction equation

HRID 1931026 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][NH:7][C:8]2=[O:11])=[CH:4][CH:3]=1.[CH:12]([O:15][C:16]1[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][C:17]=1[C:18](O)=[O:19])([CH3:14])[CH3:13]>N1C=CC=CC=1.CN(C)C1C=CN=CC=1.ClCCl>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][N:7]([C:18](=[O:19])[C:17]3[CH:21]=[C:22]([S:25]([CH3:28])(=[O:26])=[O:27])[CH:23]=[CH:24][C:16]=3[O:15][CH:12]([CH3:13])[CH3:14])[C:8]2=[O:11])=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 124964756-Chloro-2,3-dihydro-1H-isoindol-1-oneHCID 211002372-Isopropoxy-5-methylsulfonylbenzoic acid

Product 1

HCID 57753529HCID 57753529, compoundYield 55%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent
HCID 6344
Dichloromethane
Solvent

Procedure

0.4 mmol 6-chloro-1-isoindolinone (CAS: 58083-59-3) was dissolved in 3 ml of pyridine. 0.05 mmol of 4-dimethylaminopyridine was added, followed by slow addition of a solution of 0.5 mmol 2-isopropoxy-5-methanesulfonyl-benzoyl chloride (prepared from example B1 and oxalyl chloride in dichloromethane) in 2 ml dichloromethane at room temperature. The reaction mixture is stirred for 10 minutes at room temperature, then the dichloromethane is stripped off in the rotatory evaporator. The remaining solution was then refluxed for 3 hours. The dark red solution was quenched with water, acidified by addition of diluted hydrochloric acid and extracted 3 times with ethyl acetate. The organic phase is dried and concentrated. Chromatography (silica gel; ethyl acetate/heptane) gave the title compound as a slightly yellowish solid. Yield=55%. MS (m/e): 408.2 [M+H]+, 100%).

Workup

  1. customthe dichloromethane is stripped off in the rotatory evaporator
  2. temperatureThe remaining solution was then refluxed for 3 hours
  3. customThe dark red solution was quenched with water
  4. additionacidified by addition of diluted hydrochloric acid
  5. extractionextracted 3 times with ethyl acetate
  6. customThe organic phase is dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0a4acb00b837463e8be889b90c524005
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08188139B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes