Hydrazine hydrate (1:1) → HCID 22563509, compound

HRID 2249609Notes

Reaction equation

HRID 2249609 reaction equation
[CH3:1][C:2]1[NH:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][N:15]1C(=O)C2C(=CC=CC=2)C1=O.O.NN>C(O)C>[CH3:1][C:2]1[NH:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][NH2:15]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 22563291HCID 22563291, compound

Product 1

HCID 22563509HCID 22563509, compoundYield 118%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-[2-(5-methyl-2-phenyl-1H-imidazol-4-yl)-ethyl]-isoindole-1,3-dione (5.3 g) in ethanol (80 ml) was added hydrazine hydrate (4.0 g). The reaction mixture was stirred under reflux for 4 h, cooled to 0° C., and the precipitate was filtered off. To the filtrate was added brine and cold 2N NaOH (20 ml), and the mixture was extracted with ethyl acetate. The organic phase was washed with brine, dried over magnesium sulphate and evaporated to dryness in high vacuum to obtain 2-(5-methyl-2-phenyl-1H-imidazol-4-yl)-ethylamine (3.8 g) as an off-white solid, which was sufficiently pure to be used directly in the next step.

Workup

  1. temperatureunder reflux for 4 h
  2. filtrationthe precipitate was filtered off
  3. additionTo the filtrate was added brine and cold 2N NaOH (20 ml)
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic phase was washed with brine
  6. dry with materialdried over magnesium sulphate
  7. customevaporated to dryness in high vacuum

Sources & evidence

ORD record
ord-b964c44e52284cd3a6af395cb7ad3b96
Source dataset
uspto-grants-2008_01
Patent number
US07314884B2

Reaction notes

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