2-Hydrazinopyridine → HCID 21812346, compound

HRID 1253473

Reaction equation

HRID 1253473 reaction equation
C[N:2]([CH3:8])/[CH:3]=[CH:4]/[C:5](=O)[CH3:6].[NH:9]([C:11]1[CH:16]=[CH:15][CH:14]=CN=1)[NH2:10]>C(O)C>[CH3:14][C:15]1[CH:16]=[CH:11][N:9]([C:8]2[CH:6]=[CH:5][CH:4]=[CH:3][N:2]=2)[N:10]=1

Participants

4

Reactant 2

HCID 786452-HydrazinopyridineHCID 5369152trans-4-(Dimethylamino)-3-buten-2-one

Product 1

HCID 21812346HCID 21812346, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

(3E)-4-(dimethylamino)but-3-en-2-one (255 mg, 2.25 mmol) and 2-hydrazinopyridine (369 mg, 3.38 mmol) were added to ethanol (3 ml). The reaction mixture was heated to 150° C. in the Biotage Initiator Series microwave reactor. After 30 minutes, the reaction mixture was cooled and concentrated. The residue was purified by column chromatography on silica gel, (ethyl acetate/isohexane gradient) to afford 2-(3-methyl-1H-pyrazol-1-yl)pyridine (faster eluting isomer) and 2-(5-methyl-1H-pyrazol-1-yl)pyridine (slower eluting isomer).

Workup

  1. temperaturethe reaction mixture was cooled
  2. concentrationconcentrated
  3. customThe residue was purified by column chromatography on silica gel, (ethyl acetate/isohexane gradient)

Sources & evidence

ORD record
ord-a72bebeb7f854f1b842f3b83f614b6b8
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Linked notes

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