Hydrazine hydrate (1:1) → (2E)-3-(4-tert-butylphenyl)-3-(5-chloro-6-methoxypyridin-2-yl)prop-2-en-1-amine

HRID 70706Notes

Reaction equation

HRID 70706 reaction equation
O.NN.[C:4]([C:8]1[CH:13]=[CH:12][C:11](/[C:14](/[C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([O:35][CH3:36])[N:29]=2)=[CH:15]\[CH2:16][N:17]2C(=O)C3C(=CC=CC=3)C2=O)=[CH:10][CH:9]=1)([CH3:7])([CH3:6])[CH3:5]>C(O)C.[Cl-].[Na+].O>[C:4]([C:8]1[CH:13]=[CH:12][C:11](/[C:14](/[C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([O:35][CH3:36])[N:29]=2)=[CH:15]\[CH2:16][NH2:17])=[CH:10][CH:9]=1)([CH3:7])([CH3:5])[CH3:6]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67398370HCID 67398370, compound

Product 1

HCID 67400678(2E)-3-(4-tert-butylphenyl)-3-(5-chloro-6-methoxypyridin-2-yl)prop-2-en-1-amine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Hydrazine monohydrate (13 μL) was added to a solution of 2-[(2E)-3-(4-tert-butylphenyl)-3-(5-chloro-6-methoxypyridin-2-yl)prop-2-en-1-yl]-1H-isoindole-1,3(2H)-dione (98 mg) in ethanol. Thereafter, the mixture was stirred with heating under reflux for three hours and then stirred at room temperature overnight. Brine was added to the reaction solution, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate and filtered, after which the solvent was evaporated under reduced pressure to give a crude product of (2E)-3-(4-tert-butylphenyl)-3-(5-chloro-6-methoxypyridin-2-yl)prop-2-en-1-amine.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for three hours
  3. stirringstirred at room temperature overnight
  4. extractionfollowed by extraction with chloroform
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customafter which the solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-3d581e25f87646a4b58c552ec8c5e56a
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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