Hydrochloric Acid → HCID 67045281, compound

HRID 1023686Notes

Reaction equation

HRID 1023686 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[N:8]([C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH3:22])=[CH:16][CH:15]=1)[C:7]2=[O:23])([O-])=O.[Sn].Cl.[OH-].[Na+]>C(O)C>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[N:8]([C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH3:22])=[CH:16][CH:15]=1)[CH2:7]2.[NH2:1][C:4]1[CH:5]=[C:6]2[C:10]([CH2:9][N:8]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH3:22])=[CH:16][CH:15]=3)[C:7]2=[O:23])=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5352426Tin atomHCID 67045729HCID 67045729, compound

Product 2

HCID 67045281HCID 67045281, compoundHCID 67045313HCID 67045313, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

A solution of 5-nitro-2-(4-propyl-phenyl)-isoindole-1,3-dione (3.11 g, 10.03 mmol) obtained in Example 1 and tin (16.66 g, 140.39 mmol) in ethanol (125 ml) was added with concentrated hydrochloric acid (74 ml), and the mixture was stirred with heating at 75° C. for 8 hours. The reaction solution was cooled to room temperature, and then added to 2 N aqueous sodium hydroxide (220 ml), and the mixture was filtered through Cerite. The filtrate was added with chloroform for extraction. The chloroform layer was washed with saturated brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:ethyl acetate=30:1) and recrystallization (ethanol) to obtain the objective compounds, 5-amino-2-(4-propyl-phenyl)-isoindol-1-one as a pale yellow powdery substance (1.13 g, yield: 42.3%) and 6-amino-2-(4-propyl-phenyl)-isoindol-1-one as a pale yellow powdery substance (0.27 g, yield: 10.2%).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. filtrationthe mixture was filtered through Cerite
  3. additionThe filtrate was added with chloroform for extraction
  4. washThe chloroform layer was washed with saturated brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (chloroform:ethyl acetate=30:1) and recrystallization (ethanol)

Sources & evidence

ORD record
ord-402e4512f73240c8aa344f0a10f2da10
Source dataset
uspto-grants-2014_05
Patent number
US08722723B2

Reaction notes

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