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

HRID 1943333Notes

Reaction equation

HRID 1943333 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-a275b599a1cc477cad401d9f5813fa15
Source dataset
uspto-grants-2013_03
Patent number
US08389771B2

Reaction notes

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