Hydrazine → (4-Bromo-2-ethylphenyl)methanamine

HRID 859690Notes

Reaction equation

HRID 859690 reaction equation
[Br:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][N:7]2C(=O)C3C(=CC=CC=3)C2=O)=[C:4]([CH2:20][CH3:21])[CH:3]=1.NN>C(Cl)(Cl)Cl.C(O)C>[Br:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][NH2:7])=[C:4]([CH2:20][CH3:21])[CH:3]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 587642872-(4-Bromo-2-ethyl-benzyl)-isoindole-1,3-dione

Product 1

HCID 58764124(4-Bromo-2-ethylphenyl)methanamine

Reagents, catalysts & solvents 1

HCID 21889567Chloroform ethanolSolvent

Procedure

2-(4-Bromo-2-ethyl-benzyl)-isoindole-1,3-dione (4 g, 11.7 mmol) and hydrazine (1.8 mL, 58.3 mmol) in chloroform:ethanol (1:1.5, 250 mL) were refluxed for 4 h. The mixture was cooled to room temperature and filtered through a pad of celite. The solution was diluted in water and partitioned. The organic layer was washed with water, saturated sodium bicarbonate, then saturated sodium chloride, dried (Na2SO4), filtered, and then concentrated in vacuo to a yellow oil (2.2 g, 88%). 1H NMR (300 MHz, CDCl3): δ ppm 1.23 (t, J=7.54 Hz, 3 H) 1.65 (s, 2 H) 2.66 (q, J=7.60 Hz, 2 H) 3.84 (s, 2 H) 7.19–7.23 (m, 1 H) 7.30–7.34 (m, 2 H).

Workup

  1. filtrationfiltered through a pad of celite
  2. additionThe solution was diluted in water
  3. custompartitioned
  4. washThe organic layer was washed with water, saturated sodium bicarbonate
  5. dry with materialsaturated sodium chloride, dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo to a yellow oil (2.2 g, 88%)

Sources & evidence

ORD record
ord-d8062c2e63db40a9a796a7cb8eb892d6
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

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