Hydrazine hydrate (1:1) → HCID 57608473, compound

HRID 517111Notes

Reaction equation

HRID 517111 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]#[C:10][C:11]1[CH:12]=[C:13]([CH2:17][CH2:18][CH2:19][N:20]2C(=O)C3C(=CC=CC=3)C2=O)[CH:14]=[CH:15][CH:16]=1.O.NN>CCO>[CH3:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[C:9]#[C:10][C:11]1[CH:12]=[C:13]([CH2:17][CH2:18][CH2:19][NH2:20])[CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)2×HCID 57608529HCID 57608529, compound

Product 1

HCID 57608473HCID 57608473, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(3-(3-((2,6-dimethylphenyl)ethynyl)phenyl)propyl)isoindoline-1,3-dione (13) (0.094 g, 0.24 mmol) and hydrazine hydrate (0.038 g, 0.75 mmol) in dry EtOH (5 mL) was heated under reflux for 3 h. Additional hydrazine hydrate (0.038 g, 0.75 mmol) was added and heating continued for a further 4 h. The solvent was removed under reduced pressure and the residue was sonicated in a mixture of hexanes and aqueous Na2SO4. The mixture was filtered through Celite and washed with hexanes. The organic layer was concentrated under reduced pressure. Purification by flash chromatography (10:1:9 EtOAc/7 M NH3 in MeOH/hexanes) gave 3-(3-((2,6-dimethylphenyl)ethynyl)phenyl)propan-1-amine as a colorless oil. Yield (0.015 g, 25%): 1H NMR (400 MHz, DMSO-d6) δ 7.32-7.39 (m, 3H), 7.25 (m, 1H), 7.13-7.22 (m, 3H), 2.65 (t, J=7.6 Hz, 2H), 2.54 (t, J=7.2 Hz, 2H), 2.46 (s, 6H), 1.61-1.69 (m, 2H), 1.40 (br s, 2H).

Workup

  1. temperatureunder reflux for 3 h
  2. temperatureheating
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was sonicated in a mixture of hexanes and aqueous Na2SO4
  5. filtrationThe mixture was filtered through Celite
  6. washwashed with hexanes
  7. concentrationThe organic layer was concentrated under reduced pressure
  8. customPurification by flash chromatography (10:1:9 EtOAc/7 M NH3 in MeOH/hexanes)

Sources & evidence

ORD record
ord-ae42cbdfc15141afaac2498e153bea71
Source dataset
uspto-grants-2015_08
Patent number
US09115056B2

Reaction notes

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