Hydrochloric Acid → HCID 67436541, compound

HRID 1663231Notes

Reaction equation

HRID 1663231 reaction equation
Cl.[O:2]=[C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[N:4]1[CH2:13][CH2:14][C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=1.[CH2:23](N)[CH2:24][NH2:25]>C(O)C>[NH:20]1[CH2:23][CH2:24][N:25]=[C:19]1[C:18]1[CH:17]=[CH:16][C:15]([CH2:14][CH2:13][N:4]2[C:3](=[O:2])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]2=[O:12])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3301EthylenediamineHCID 674369234-[2-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]benzonitrile

Product 1

HCID 67436541HCID 67436541, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dry hydrogen chloride gas was bubbled through an ice cold solution of 4-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-benzonitrile (7.83 g, 28.3 mmol) in ethanol (400 mL) for 3 h, then the so obtained mixture was kept at 8° C. overnight. The reaction mixture was concentrated in vacuo, the residue was dissolved in dry ethanol (400 mL), ethylenediamine (2.0 mL, 29.7 mmol) was added and the reaction mixture was stirred at room temperature overnight. The mixture was concentrated in vacuo, the residue was partitioned between dichloromethane (400 mL) and concentrated ammonium hydroxide (400 mL), the phases were separated and the water phase was extracted with dichloromethane (2×200 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated. The crude product was recrystallized from 2-propanol to yield 5.58 g (62%) of the title compound as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in dry ethanol (400 mL)
  3. concentrationThe mixture was concentrated in vacuo
  4. customthe residue was partitioned between dichloromethane (400 mL) and concentrated ammonium hydroxide (400 mL)
  5. customthe phases were separated
  6. extractionthe water phase was extracted with dichloromethane (2×200 mL)
  7. dry with materialThe combined organic layers were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product was recrystallized from 2-propanol

Sources & evidence

ORD record
ord-b77423716e3645508e69277aa65255f9
Source dataset
uspto-grants-2011_10
Patent number
US08034827B2

Reaction notes

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