HCID 13986697, compound → HCID 13986699, compound

HRID 2309698Notes

Reaction equation

HRID 2309698 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[NH:3]1.[CH3:12][CH2:13][C:14](Cl)=[O:15].[CH3:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:19]=1[NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]1[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=1>ClCCl.O.[OH-].[Na+]>[CH3:24][C:20]1[CH:21]=[CH:22][CH:23]=[C:18]([CH3:17])[C:19]=1[N:25]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]1[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=1)[C:14](=[O:15])[CH:13]([CH3:12])[N:3]1[C:4](=[O:11])[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2]1=[O:1]

Participants

6

Reactant 2

HCID 13986697HCID 13986697, compoundHCID 131715265HCID 131715265, compound

Product 1

HCID 13986699HCID 13986699, compoundYield 67.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 1.7 g of 2,3-dihydro-1,3-dioxo-1H-isoindole-alpha-methyl-acetyl chloride in 20 ml of dry dichloromethane was added dropwise to a solution of 2.0 g N-(2,6-dimethylphenyl)-3-pyridinehexanamine in 20 ml of dichloromethane. The reaction mixture was stirred overnight at room temperature, diluted with water and aqueous sodium hydroxide and the layers were separated. The aqueous layer was extracted with dichloromethane and the combined organic layers were washed with water, dried with potassium carbonate and concentrated. The residue was crystallized from ethyl acetate-hexane to give 2.3 g of rac.-2,3-dihydro-N-(2,6-dimethylphenyl)-alpha-methyl-1,3-dioxo-N-[6-(3-pyridinyl)hexyl]-1H-isoindole-2-acetamide, mp 113°-115° C.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with dichloromethane
  3. washthe combined organic layers were washed with water
  4. dry with materialdried with potassium carbonate
  5. concentrationconcentrated
  6. customThe residue was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-c743a3c235554c8f9b867ad9d947367e
Source dataset
uspto-grants-1987_09
Patent number
US04696930

Reaction notes

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