Hydrazine → Methyl 1-(6-hydrazinopyridin-3-yl)cyclopropanecarboxylate

HRID 2245949Notes

Reaction equation

HRID 2245949 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]2([C:11]([O:13][CH3:14])=[O:12])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[NH2:15][NH2:16]>N1C=CC=CC=1>[NH:15]([C:2]1[N:7]=[CH:6][C:5]([C:8]2([C:11]([O:13][CH3:14])=[O:12])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1)[NH2:16]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 59216284Methyl 1-(6-chloro-3-pyridinyl)cyclopropanecarboxylate

Product 1

HCID 59216299Methyl 1-(6-hydrazinopyridin-3-yl)cyclopropanecarboxylateYield 90%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of methyl 1-(6-chloropyridin-3-yl)cyclopropanecarboxylate (1 g, 0.005 mol) in pyridine (2 mL) was added hydrazine (0.30 mL, 0.0094 mol). The solution was heated at 90° C. overnight. The reaction solution was cooled to RT, and then diluted with a small amount of ice-water. The precipitate was collected by filtration, and dried under vacuum to afford the desired compound (0.9 g, 90%). Analytical LCMS: (M+H)+=208.0.

Workup

  1. temperatureThe reaction solution was cooled to RT
  2. filtrationThe precipitate was collected by filtration
  3. customdried under vacuum

Sources & evidence

ORD record
ord-b090866f38e54014a2888eff49ec2ce4
Source dataset
uspto-grants-2010_03
Patent number
US07683060B2

Reaction notes

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