Hydrazine hydrate (1:1) → 1-amino-3,3-bis(4-pyridinylmethyl)-1,3-dihydro-2H-indol-2-one

HRID 53946Notes

Reaction equation

HRID 53946 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]2([CH2:26][C:27]3[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=3)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([N:17]=CC3C=CC=CC=3)[C:9]2=[O:25])=[CH:3][CH:2]=1.O.NN>C(O)C>[NH2:17][N:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([CH2:7][C:4]2[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=2)([CH2:26][C:27]2[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=2)[C:9]1=[O:25]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 540280563,3-bis-(4-pyridinylmethyl)-1,3-dihydro-1-[(phenylmethylene)amino]-2H-indol-2-one

Product 1

HCID 149942721-amino-3,3-bis(4-pyridinylmethyl)-1,3-dihydro-2H-indol-2-oneYield 40.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution consisting of 3,3-bis-(4-pyridinylmethyl)-1,3-dihydro-1-[(phenylmethylene)amino]-2H-indol-2-one (7.84 g) and absolute ethanol (68 ml) was added hydrazine hydrate (6.4 ml). The resulting mixture was heated at reflux for 5.75 hours, followed by cooling to 0° C. The product crystallized upon cooling. Filtration and washing with ether-pentane afforded 2.50 g of 1-amino-3,3-bis(4-pyridinylmethyl)-1,3-dihydro-2H-indol-2-one.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 5.75 hours
  3. customThe product crystallized
  4. temperatureupon cooling
  5. filtrationFiltration
  6. washwashing with ether-pentane

Sources & evidence

ORD record
ord-4a4459d3a7134efe8cf6b2e21b46da3a
Source dataset
uspto-grants-1997_04
Patent number
US05621116

Reaction notes

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